Triarylamine compound containing condensed ring and organic light-emitting device thereof

文档序号：1810292 发布日期：2021-11-09 浏览：16次中文

阅读说明：本技术 一种含稠环的三芳胺类化合物及其有机发光器件 (Triarylamine compound containing condensed ring and organic light-emitting device thereof ) 是由李梦茹刘喜庆陆影韩春雪于 2021-08-12 设计创作，主要内容包括：本发明提供一种含稠环的三芳胺类化合物及其有机发光器件,涉及有机光电材料技术领域。本发明含稠环的三芳胺类化合物具有优异的空穴传输性能,具有发光效率高、驱动电压低的优点,是良好的空穴传输材料,能够提高有机发光器件的发光效率、使用寿命以及降低器件的驱动电压；并且本发明提供的含稠环的三芳胺类化合物作为覆盖层材料应用于有机发光器件中,能够提高光取出效率,从而提高有机发光器件的发光效率,同时也能够延长器件的寿命。本发明的三芳胺类有机化合物合成简单易操作,可广泛应用于面板显示、照明光源、有机太阳能电池、有机感光体或有机薄膜晶体管等领域。(The invention provides a triarylamine compound containing condensed rings and an organic light-emitting device thereof, and relates to the technical field of organic photoelectric materials. The triarylamine compound containing condensed rings has excellent hole transport performance, has the advantages of high luminous efficiency and low driving voltage, is a good hole transport material, and can improve the luminous efficiency and the service life of an organic light-emitting device and reduce the driving voltage of the device; the triarylamine compound containing the condensed ring is applied to the organic light-emitting device as a covering layer material, and can improve the light extraction efficiency, thereby improving the light-emitting efficiency of the organic light-emitting device and prolonging the service life of the device. The triarylamine organic compound is simple to synthesize and easy to operate, and can be widely applied to the fields of panel display, lighting sources, organic solar cells, organic photoreceptors or organic thin film transistors and the like.)

1. A triarylamine compound containing condensed rings is characterized in that the molecular structure is shown as formula I:

wherein the group C is selected from one of the following groups:

wherein, R is₂The same or different is selected from hydrogen, deuterium, phenyl or naphthyl;

the R is₁One selected from hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 cycloalkyl group, a substituted or unsubstituted C6-C25 aryl group and a substituted or unsubstituted C2-C20 heteroaryl group;

c is selected from 0 or 1; k is selected from 0, 1 or 2; i is selected from 0, 1, 2 or 3; j is selected from 0, 1, 2, 3, 4, 5, 6 or 7; d is selected from 0, 1, 2, 3 or 4; h is selected from 0, 1, 2, 3, 4 or 5; e is selected from 0, 1, 2, 3, 4, 5 or 6; f is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; g is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;

The group B is selected from one of the following groups:

wherein R is_mAre the same or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, and substituted or unsubstituted C6-C25 arylAnd a substituted or unsubstituted heteroaryl group having from C2 to C20;

m is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; r is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11;

ar is selected from any one of the following groups:

the R is₁₂Selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl or selected from substituted or unsubstituted aromatic ring and aliphatic ring fused ring group; the R is₁₃Selected from deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C2-C20 heteroaryl;

Wherein said R₁₃Can also be substituted by R₂₃Substituted, R₂₃One or more groups selected from hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, phenyl, pentadeuterated phenyl, deuterated naphthyl, tolyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, dibenzothienyl, dibenzofuranyl, and, in the case of substitution with a plurality of substituents, the plurality of substituents may be the same as or different from each other;

a is 0, 1, 2, 3 or 4; b is 1, 2, 3, 4 or 5; p is 0, 1, 2, 3, 4, 5, 6, 7 or 8; q is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;

said L₀、L₁、L₂Independently selected from a single bond, substituted or unsubstituted arylene of C6-C25, substituted or unsubstituted heteroarylene of C2-C20;

wherein "substituted …" in the above "substituted or unsubstituted …" means being substituted with one or more substituents independently selected from the group consisting of deuterium, cyano, alkyl group of C1 to C15, cycloalkyl group of C3 to C15, aryl group of C6 to C25, and heteroaryl group of C2 to C20.

2. A triarylamine compound containing fused rings according to claim 1 wherein R is_mThe same or different from each other, and each is independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, norbornyl, or one of the groups shown below:

3. a triarylamine compound containing fused rings according to claim 1 wherein the group C is selected from one of the following groups:

4. a triarylamine compound containing fused rings according to claim 1 wherein R is₁₂Selected from methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, phenyl, tolyl, biphenyl, naphthyl or one of the following substituents:

5. triarylamines containing fused rings according to claim 1A compound characterized in that L is₀、L₁、L₂Independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted anthrylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenylene, and substituted or unsubstituted phenylene-naphthylene, wherein the substituent is one or more of deuterium, ethyl, isopropyl, tert-butyl, phenyl, and pentadeuterated phenyl, and in the case of substitution with a plurality of substituents, the plurality of substituents are the same as or different from each other.

6. A triarylamine compound containing fused rings according to claim 1 wherein L is₀、L₁、L₂Independently selected from a single bond or one of the following groups:

7. a triarylamine compound containing fused rings according to claim 1, wherein the triarylamine compound containing fused rings is selected from any one of the following chemical structures:

8. an organic light-emitting device comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes selected from the anode and the cathode, and wherein the organic layer contains any one or a combination of at least two of the triarylamine compounds having a condensed ring according to any one of claims 1 to 7.

9. An organic light-emitting device according to claim 8, wherein the organic layer comprises a hole transport layer containing any one or a combination of at least two of the triarylamine compound having a condensed ring according to any one of claims 1 to 7.

10. The organic light-emitting device according to claim 8, wherein the organic layer comprises a cover layer containing any one or a combination of at least two of the triarylamine-based compounds having a condensed ring according to any one of claims 1 to 7.

Technical Field

The invention relates to the technical field of organic photoelectric materials, in particular to a triarylamine compound containing condensed rings and an organic light-emitting device thereof.

Background

With the advent of the 5G ultra-high speed network communication era, the human demand for information will increase explosively, and the requirements for randomness and timeliness of information acquisition will become higher and higher. Portable, large-size display technology is a prerequisite to meet this demand. In view of the current technical development, an organic light-emitting diode (OLED) using an organic semiconductor as a functional material has the most potential, which is attributed to the fact that the OLED technology has the advantages of wide viewing angle, fast response speed, energy saving, stable color, strong environmental adaptability, no radiation, light weight, thin thickness, wide adaptable display temperature range, and the like, and particularly, a device can be manufactured on a flexible substrate, so that large-area display and portability become possible.

An organic light emitting device is a self light emitting device utilizing the following principle: by applying an electric field, the fluorescent substance emits light by the recombination energy of holes injected from the anode and electrons injected from the cathode. OLED organic light-emitting materials can be broadly classified into three types of materials in terms of use: the light-emitting diode comprises a charge injection and transmission material, a light-emitting material and a covering layer material for improving the light-emitting efficiency, further, the charge injection and transmission material is divided into an electron injection material, an electron transmission material, a hole injection material and a hole transmission material, and the light-emitting material can also be divided into a main body light-emitting material and a doping material.

The organic hole transport layer plays an important role in transferring holes injected from the anode to the light emitting layer, and the hole transport layer material with excellent hole mobility is beneficial to the injection balance of carriers in the device, so that the driving voltage of the organic light emitting device is reduced. On the other hand, in order to prevent excitons generated in the light-emitting layer from diffusing into the hole transport layer, which causes color cast and reduction of light-emitting efficiency, the hole transport layer is also required to be capable of blocking the excitons from diffusing out, preventing efficiency roll-off and improving the stability of the device.

However, research on organic light emitting materials has been widely conducted in academia and industry, and a large number of organic light emitting materials having excellent properties have been developed. In view of the above, the future direction of organic light emitting devices is to develop high efficiency, long lifetime, low cost white light devices and full color display devices, but the industrialization of this technology still faces many key issues. Therefore, designing and searching a stable and efficient compound as a novel material of an organic light-emitting device to overcome the defects of the organic light-emitting device in the practical application process is a key point in the research work of the organic light-emitting device material and the future research and development trend.

Disclosure of Invention

The invention aims to provide a triarylamine compound containing condensed rings and an organic light-emitting device thereof on the basis of the prior art and aiming at industrialization, and the organic light-emitting device prepared by using the triarylamine compound containing condensed rings solves the problem of unmatched electron/hole migration in an organic material layer, thereby obviously improving the comprehensive performance of the device in the aspects of luminous efficiency, voltage and the like; the organic light-emitting device solves the problems by being used as a main composition of a hole transport layer in the organic light-emitting device, and the molecular structure general formula of the organic light-emitting device is shown as the formula I:

wherein the group C is selected from one of the following groups:

wherein, R is₂The same or different is selected from hydrogen, deuterium, phenyl or naphthyl;

The group B is selected from one of the following groups:

wherein R is_mAre the same or different from each other, and are each independently selected from one of hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group of C1 to C15, a substituted or unsubstituted cycloalkyl group of C3 to C15, a substituted or unsubstituted aryl group of C6 to C25, and a substituted or unsubstituted heteroaryl group of C2 to C20;

m is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; r is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11;

ar is selected from any one of the following groups:

the R is₁₂Selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstitutedThe heteroaryl of C2-C20 or a condensed ring group selected from a substituted or unsubstituted aromatic ring and an aliphatic ring; the R is₁₃Selected from deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C2-C20 heteroaryl;

a is 0, 1, 2, 3 or 4; b is 1, 2, 3, 4 or 5; p is 0, 1, 2, 3, 4, 5, 6, 7 or 8; q is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;

said L₀、L₁、L₂Independently selected from a single bond, substituted or unsubstituted arylene of C6-C25, substituted or unsubstituted heteroarylene of C2-C20;

The invention also provides an organic light-emitting device which comprises an anode, a cathode and an organic layer, wherein the organic layer is positioned between the anode and the cathode or positioned at the outer side of more than one of the anode and the cathode, and the organic layer contains any one or the combination of at least two of the triarylamine compounds containing condensed rings.

The invention has the beneficial effects that:

the invention provides a triarylamine compound containing condensed rings and an organic light-emitting device thereof. The compound provided by the invention has higher HOMO energy level and high hole injection efficiency, is beneficial to the transmission of current carriers, and can effectively improve the exciton utilization rate, thereby improving the luminous efficiency and the service life of an organic light-emitting device and reducing the driving voltage of the device;

The triarylamine compound containing condensed rings provided by the invention is applied to an organic light-emitting device as a covering layer material, can effectively solve the problem of total emission of an interface of an ITO film and a glass substrate and an interface of the glass substrate and air, reduces total reflection loss and waveguide loss in the OLED device, and improves light extraction efficiency, thereby improving the light-emitting efficiency of the organic light-emitting device. In addition, the triarylamine compound containing the condensed ring effectively blocks water and oxygen in the external environment, protects the OLED display panel from being corroded by water and oxygen, and can prolong the service life of devices.

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.

In the present specification, when the position of a substituent on an aromatic ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the aromatic ring. For example, Can representAnd so on.

The alkyl group in the present invention refers to a hydrocarbon group obtained by dropping one hydrogen atom from an alkane molecule, and may be a straight-chain alkyl group or a branched-chain 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, isopropyl, isobutyl, sec-butyl, tert-butyl, the isomeric form of n-pentyl, the isomeric form of n-hexyl, the isomeric form of n-heptyl, the isomeric form of n-octyl, the isomeric form of n-nonyl, the isomeric form of n-decyl, and the like. 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, or a tert-butyl group.

The cycloalkyl group in the present invention refers to a hydrocarbon group obtained by removing one hydrogen atom from a cycloalkane molecule, and preferably has 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 6 carbon atoms, and examples thereof may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, bornyl, norbornyl, and the like. The cycloalkyl group is preferably a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group or a norbornyl 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, and preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 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, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms, 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 alkenyl group in the present invention means a monovalent group obtained by removing one hydrogen atom from an olefin molecule, and includes a monoalkenyl group, a dienyl group, a polyalkenyl group, and the like. Preferably from 2 to 60 carbon atoms, more preferably from 2 to 30 carbon atoms, particularly preferably from 2 to 15 carbon atoms, most preferably from 2 to 6 carbon atoms. Examples of the alkenyl group include vinyl, butadienyl and the like, but are not limited thereto. The alkenyl group is preferably a vinyl group.

The arylene group in the present invention refers to a general term of divalent groups remaining after two hydrogen atoms are removed from the aromatic core carbon of the aromatic compound molecule, and may be monocyclic arylene group, polycyclic arylene group or condensed ring arylene group, and preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 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, particularly preferably 6 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms, the linking site of the heteroarylene group may be located on a ring-forming carbon atom or on 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, phenoxathiin group.

The term "substituted …" as used herein, such as substituted alkyl, substituted cycloalkyl, substituted alkenyl, substituted aryl, substituted heteroaryl, substituted arylene, substituted heteroarylene, etc., means mono-or polysubstituted with groups independently selected from, but not limited to, deuterium, halogen, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, substituted or unsubstituted amine, etc., preferably with groups selected from, deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, cyclopropyl, cyclohexyl, adamantyl, norbornanyl, phenyl, tolyl, mesityl, penta-deuterated phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, benzophenanthryl, biphenyl, etc, Pyrenyl, benzyl, triphenylene, pyrenyl, phenyl, or phenyl,A phenyl group, a perylene group, a fluoranthenyl group, a fluorenyl group, a 9, 9-dimethylfluorenyl group, a 9, 9-diphenylfluorenyl group, a 9-methyl-9-phenylfluorenyl group, a spirobifluorenyl group, a dianilino group, a dimethylamino group, a carbazolyl group, a 9-phenylcarbazolyl group, a carbazolonyl group, a pyrrolyl group, a furyl group, a thienyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, a dibenzothienyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, an oxazolyl group, a thiazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzotriazolyl group, a benzimidazolyl group, an indolyl group, a quinolyl group, an isoquinolyl group, a phenothiazinyl group Mono-or polysubstituted with respect to the radicals phenoxazinyl, acridinyl.

Aliphatic in the context of the present invention means aliphatic hydrocarbons having from 1 to 60 carbon atoms, which may be fully or partially unsaturated.

The alicyclic ring in the present invention refers to cyclic hydrocarbon having aliphatic property, which contains closed carbon ring in the molecule, and may be monocyclic hydrocarbon or polycyclic hydrocarbon formed by 3-18, preferably 3-12, more preferably 3-7 carbon atoms, and may be fully unsaturated or partially unsaturated, such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, cycloheptene, etc., but is not limited thereto. Multiple monocyclic hydrocarbons can also be linked in a variety of ways: two rings in the molecule can share one carbon atom to form a spiro ring; two carbon atoms on the ring can be connected by a carbon bridge to form a bridged ring; several rings may also be interconnected to form a cage-like structure.

The term "ring" as used herein, unless otherwise specified, refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms or an aromatic ring having 6 to 60 carbon atoms or a heterocyclic ring having 2 to 60 carbon atoms or a combination thereof, which contains a saturated or unsaturated ring.

The bonding to form a cyclic structure according to the present invention means that the two groups are linked to each other by a chemical bond and optionally aromatized. As exemplified below:

In the present invention, the ring formed by the connection may be a five-membered ring or a six-membered ring or a fused ring, such as benzene, naphthalene, fluorene, cyclopentene, cyclopentane, cyclohexane acene, quinoline, isoquinoline, dibenzothiophene, phenanthrene or pyrene, but not limited thereto.

The invention provides a triarylamine compound containing condensed rings, which has a molecular structure general formula shown as formula I:

wherein the group C is selected from one of the following groups:

wherein, R is₂The same or different is selected from hydrogen, deuterium, phenyl or naphthyl;

The group B is selected from one of the following groups:

m is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; r is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11;

ar is selected from any one of the following groups:

a is 0, 1, 2, 3 or 4; b is 1, 2, 3, 4 or 5; p is 0, 1, 2, 3, 4, 5, 6, 7 or 8; q is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;

said L₀、L₁、L₂Independently selected from a single bond, substituted or unsubstituted arylene of C6-C25, substituted or unsubstituted heteroarylene of C2-C20;

in the above "substituted or unsubstituted …", the term "substituted …" means that the substituted aryl group is substituted with at least one substituent independently selected from the group consisting of deuterium, a cyano group, an alkyl group having from C1 to C15, a cycloalkyl group having from C3 to C15, an aryl group having from C6 to C25, and a heteroaryl group having from C2 to C20.

Preferably, said R is _mAre identical or different from each other and are each independently selected from hydrogen, deuterium, methyl, ethyl, n-propylA group selected from the group consisting of alkyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, norbornyl, and one of the following:

preferably, said R is_mThe same or different from each other, and each is independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, norbornyl, or one of the groups shown below:

more preferably, the group B is selected from one of the following groups:

preferably, the group C is selected from one of the following groups:

preferably, said R is₁₂Selected from methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, phenyl, tolyl, biphenyl, naphthyl or one of the following substituents:

preferably, said R is₁₃Selected from deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, norbornyl, phenyl, pentadeuterated benzeneOne of a group, a deuterated naphthyl group, a tolyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a triphenylene group, an acridinyl group, a spirobifluorenyl group, a 9, 9-dimethylfluorenyl group, a 9, 9-diphenylfluorenyl group, a 9-phenylcarbazolyl group, a pyrenyl group, an indolyl group, a benzothienyl group, a benzofuranyl group, a dibenzothienyl group, a dibenzofuranyl group, or an adjacent R group ₁₃The groups may be linked to form a substituted or unsubstituted aliphatic ring.

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

preferably, said L₀、L₁、L₂Independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted anthrylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenylene, and substituted or unsubstituted phenylene-naphthylene, wherein the substituent is one or more of deuterium, ethyl, isopropyl, tert-butyl, phenyl, and pentadeuterated phenyl, and in the case of substitution with a plurality of substituents, the plurality of substituents are the same as or different from each other.

Preferably, said L₀、L₁、L₂Independently selected from a single bond or one of the following groups:

more preferably, said L₀、L₁、L₂Independently selected from a single bond or one of the following groups:

most preferably, the triarylamine compound containing a condensed ring is selected from any one of the following chemical structures:

the preparation method of the triarylamine compound containing condensed rings, which is described in formula I in the invention, can be prepared by conventional coupling reaction in the field, and can be prepared by the following synthetic route, for example, but the invention is not limited thereto:

The triarylamine compound containing condensed rings can be obtained by the conventional Buchwald reaction in the field, namely, under the nitrogen atmosphere, an amine compound a and a halogen compound b are subjected to the Buchwald reaction to obtain an intermediate A, then the intermediate A and a halogen compound c are subjected to the Buchwald reaction, and the intermediate A and the halogen compound c are reacted at corresponding temperature under corresponding catalyst, organic base, ligand and solution to obtain a corresponding compound shown in a formula I, wherein the halogen compound X is a halogen compound X₀、X₁Is Cl, Br or I.

The present invention is not particularly limited in terms of the source of the raw materials used in the above-mentioned various reactions, and can be obtained using commercially available raw materials or by a preparation method 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 compound provided by the invention has the advantages of few synthesis steps and simple method, and is beneficial to industrial production.

Preferably, the organic layer comprises a hole transport layer, and the hole transport layer contains any one or a combination of at least two of the triarylamine compounds containing condensed rings.

Preferably, the hole transport layer includes a first hole transport layer and a second hole transport layer, and the first hole transport layer and/or the second hole transport layer contains any one or a combination of at least two of the triarylamine compounds containing a condensed ring according to the present invention.

Preferably, the organic layer comprises a covering layer, and the covering layer contains any one or a combination of at least two of the triarylamine compounds containing condensed rings.

Preferably, the cover layer according to the present invention may have a single-layer structure, a two-layer structure or a multi-layer structure, and the material of the cover layer according to the present invention may be at least one selected from the group consisting of the triarylamine compound containing a fused ring according to the present invention, or may include a conventional cover layer material known to those skilled in the art.

Preferably, the organic light emitting device of the present invention is selected from the following structures, but is not limited thereto:

(1) anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/cathode/capping layer;

(2) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/cathode;

(3) anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/hole blocking layer/cathode;

(4) anode/hole transport layer/light emitting layer/electron transport layer/cathode;

(5) anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode;

(6) anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode;

(7) anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode;

(8) anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode;

(9) anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode;

(10) anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode;

(11) anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode;

(12) anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode;

(13) anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode;

(14) Anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode;

(15) anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode;

(16) anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode;

(17) anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode;

(18) anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode/capping layer;

(19) anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode;

(20) anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode;

(21) anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode;

(22) anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode;

(23) anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode/capping layer;

(24) anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode;

(25) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer;

(26) anode/hole injection layer/hole buffer layer/hole transport layer/electron blocking layer/luminescent layer/hole blocking layer/electron transport layer/electron injection layer/cathode;

(27) anode/hole injection layer/hole buffer layer/hole transport layer/electron blocking layer/luminescent layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer;

(28) anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/cathode;

(29) anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron injection layer/cathode;

(30) anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/cathode/capping layer;

(31) anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/cathode;

(32) anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron injection layer/cathode;

(33) anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/cathode/capping layer;

(34) anode/hole injection layer/hole transport layer/light emitting layer/cathode/capping layer;

(35) Anode/hole injection layer/hole transport layer/light emitting layer/cathode;

(36) anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode;

(37) anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode/capping 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 buffer layer can be added between the electron transport layer and the electron injection layer; the organic layer having the same function may be formed in a stacked structure of two or more layers, for example, the electron transport layer may have a first electron transport layer and a second electron transport layer.

The 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 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.

The anode material is preferably a material having a large work function so that holes are smoothly injected into the organic material layer, and a conductive metal oxide film, a translucent metal thin film, or the like is often used. Examples of the method for producing the film include a film (NESA or the like) made of a conductive inorganic compound containing indium oxide, zinc oxide, tin oxide, and a composite thereof, such as indium tin oxide (abbreviated as ITO) or indium zinc oxide (abbreviated as IZO), and a method using gold, platinum, silver, copper, or 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. The anode may have a laminated structure of 2 or more layers, and preferably, the anode of the present invention is formed of a transparent ITO substrate.

The hole injection layer is to improve the efficiency of hole injection from the anode into the hole transport layer and the light emitting layer. The hole injection material of the present invention 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., the hole injection layer may be a single structure made of a single substance, or a single-layer or multi-layer structure made of different substances, and the hole injection layer material may include other known materials suitable for the hole injection layer, in addition to the above materials and combinations thereof.

The hole transport layer is a layer having a function of transporting holes, and the hole transport layer may include a first hole transport layer material and a second hole transport layer material. The hole transport material of the present invention is preferably a material having a good hole transport property, and may be selected from small molecular materials such as aromatic amine derivatives, carbazole derivatives, stilbene derivatives, triphenyldiamine derivatives, styrene compounds, butadiene compounds, and polymer materials such as poly-p-phenylene derivatives, polyaniline and derivatives thereof, polythiophene and derivatives thereof, polyvinylcarbazole and derivatives thereof, polysilane and derivatives thereof, 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, 9-spirobifluorene (abbreviated as spirobifluorene-TAD) and the like, which may be a single structure composed of a single substance or a single-layer structure or a multi-layer structure formed of different substances, and the hole transport layer may include other known materials suitable for the hole transport layer in addition to the above materials and combinations thereof. More preferably, the hole transport layer is selected from any one or a combination of at least two of the triarylamine compounds containing condensed rings. .

The electron-blocking layer is a layer which transports holes and blocks electrons, and is preferably selected from N, N ' -bis (naphthalen-1-yl) -N, N ' -bis (phenyl) -2,2' -dimethylbenzidine (abbreviated as. alpha. -NPD), 4' -tris (N, N-diphenylamino) triphenylamine (abbreviated as TDATA), N ' -diphenyl-N, N ' -bis (3-methylphenyl) -1,1' -biphenyl-4, 4' -diamine (abbreviated as TPD), 4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline ] (abbreviated as TAPC), 2,7, 7-tetrakis (diphenylamino) -9, 9-spirobifluorene (abbreviated as Spiro-TAD), and the like, the electron blocking layer material may be a single structure made of a single substance, or a single-layer structure or a multi-layer structure made of different substances, and may include other known materials suitable for an electron blocking layer in addition to the above materials and combinations thereof.

The light-emitting layer is a layer having a light-emitting function. As for the light emitting layer of the organic light emitting device of the present invention, a red light emitting material, a green light emitting material, or a blue light emitting material can be used as the light emitting material, and two or more light emitting materials can be mixed and used if necessary. The light-emitting material may be a host material alone or a mixture of a host material and a dopant material, and the light-emitting layer is preferably formed using a mixture of a host material and a dopant material.

Preferably, the host material of the present invention is 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',4 ″ -tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (1-naphthyl) anthracene (α -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, such as a red light-emitting layer host material as represented below:

the guest material of the light-emitting layer of the present invention may include one material or a mixture of two or more materials, and the light-emitting material is classified into a blue light-emitting material, a green light-emitting material, and a red light-emitting material. The blue luminescent layer guest is selected from (6- (4- (diphenylamino (phenyl) -N, N-diphenylpyrene-1-amine) (DPAP-DPPA for short), 2,5,8, 11-tetra-tert-butylperylene (TBPe for short), 4' -di [4- (diphenylamino) styryl group]Biphenyl (BDAVBi for short), 4' -di [4- (di-p-tolylamino) styryl]Biphenyl (DPAVBi for short), bis (2-hydroxyphenyl pyridine) beryllium (Bepp for short) ₂) Bis (4, 6-difluorophenylpyridine-C2, N) picolinyliridium (FIrpic), and the like, and in addition to the above materials and combinations thereof, the guest material of the light-emitting layer may include other known materials suitable for use as a light-emitting layer. The green emissive guest layer is selected from tris (2-phenylpyridine) iridium (Ir (ppy)₃) Bis (2-phenylpyridine) iridium acetylacetonate (Ir (ppy)₂(acac)), and the like, the light-emitting layer guest material may include other known materials suitable for use as a light-emitting layer in addition to the above materials and combinations thereof. The red light emitting layer guest can be selected from 9, 10-di [ N- (p-tolyl) anilino]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, the red-emitting layer guest material may include, in addition to the above materials, other known materials suitable for use as a light-emitting layer, such as one of the red-emitting layer guest materials represented below:

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

The hole blocking layer is a layer that transports electrons and blocks holes, and is preferably selected from 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (abbreviated as BCP), 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (abbreviated as TPBi), and tris (8-hydroxyquinoline) aluminum (III) (abbreviated as 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), and the like, which may be a single structure composed of a single substance or a single-layer structure or a multi-layer structure composed of different substances. In addition to the above materials, the hole blocking layer material may include other known materials suitable for use as a hole blocking layer.

The electron transport layer is a layer having a function of transporting electrons, and plays a role of injecting electrons and balancing carriers, and the electron transport layer may include a first electron transport layer material and a second electron transport layer material. The electron transport material can be selected from metal complexes of known oxadiazole derivatives, anthraquinone dimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinone dimethane and derivatives thereof, fluorenone derivatives, diphenoquinone derivatives, 8-hydroxyquinoline and derivatives thereof, and can be a single structure formed by a single substance or a single-layer structure or a multi-layer structure formed by different substances. In addition to the above materials, the electron transport layer material may also include other known materials suitable for use as an electron transport layer.

The electron injection layer material is a material that assists the injection of electrons from the cathode into the organic layer. The best choice of material is usually a corrosion resistant high work function metal as the cathode, with Al and Ag being common materials. Electron injection materials have been developed to date and include two types; one type is an alkali metal compound, such as lithium oxide (Li)₂O), lithium boron oxide (LiBO)₂) Cesium carbonate (Cs)₂CO₃) Potassium silicate (K)₂SiO₃) And the optimal thickness is generally 0.3-1.0 nm, and the device formed by the compound can reduce the driving voltage and improve the efficiency of the device. In addition, acetate compounds of alkali metals (CH)₃COOM, where M is Li, Na, K, Rb, Cs) also have similar effects. Another class is alkali metal fluorides (MF, where M is Li, Na, K, Rb, Cs), and if Al is used as the cathode material, the optimum thickness of these materials is typically less than 1.0 nm. Preferably, the electron injection layer according to the present invention may be selected from LiF.

In the cathode material, a metal material having a small work function is generally preferable in order to inject electrons into the electron injection/transport layer or the light-emitting layer. 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. 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/□ or less, and the film thickness is usually 10nm to 1 μm, preferably 50 to 200 nm.

The covering layer material is used for reducing the total emission loss and waveguide loss in the OLED device and improving the light extraction efficiency. Alq can be used as the cover material of the invention₃TPBi or the triarylamine compound containing the condensed ring, which is disclosed by the invention, or the combination of at least two of the TPBi and the triarylamine compound.

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.

Preparation and characterization of the Compounds

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 uses British Watts G2-Si quadrupole rod series time-of-flight high resolution mass spectrometer, chloroform is used as solvent;

the elemental analysis was carried out by using a Vario EL cube type organic element analyzer of Elementar, Germany, and the sample mass was 5 to 10 mg.

EXAMPLE 1 Synthesis of Compound 4

Synthesis of intermediate A-1

To a 1L reaction flask, toluene (600mL), a-1(10.60g, 72mmol), b-1(28.61g, 72mmol), palladium acetate (0.24g, 1.08mmol), sodium tert-butoxide (13.45g, 140mmol), and tri-tert-butylphosphine (8mL in toluene) were added in that order under nitrogen. And reacted under reflux for 2 hours. After the reaction was stopped, the mixture was cooled to room temperature, filtered through celite, the filtrate was concentrated, recrystallized from methanol, filtered with suction and rinsed with methanol to give a recrystallized solid, intermediate a-1(20.71g, yield 77%) having a solid purity ≧ 99.7% by HPLC.

Synthesis of Compound 4

Under nitrogen protection, a 1L reaction flask was charged with toluene solvent (500mL), c-1(10.92g, 40mmol), intermediate A-1(14.93g, 40mmol), and Pd in that order ₂(dba)₃(0.37g, 0.40mmol), BINAP (0.75g, 1.20mmol) and sodium tert-butoxide (7.69g, 80mmol), dissolved with stirring, and reacted under reflux under nitrogen for 24 hours, after completion of the reaction, dichloromethane and distilled water were added to the reaction solution, followed by stirring and extraction with 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 the compound 4(16.75g, yield 74%), and the purity of the solid is ≧ 99.4% by HPLC. Mass spectrum m/z: 565.2756 (theoretical value: 565.2770). Theoretical element content (%) C₄₃H₃₅N: c, 91.29; h, 6.24; and N, 2.48. Measured elemental content (%): c, 91.36; h, 6.20; and N, 2.42.

EXAMPLE 2 Synthesis of Compound 9

Compound 9(20.14g) was synthesized in the same manner as in Synthesis example 1 except that c-1 was replaced with an equal mole of c-9, and the purity of the solid was ≧ 99.7% by HPLC. Mass spectrum m/z: 689.3092 (theoretical value: 689.3083). Theoretical element content (%) C₅₃H₃₉N: c, 92.27; h, 5.70; and N, 2.03. Measured elemental content (%): c, 92.20; h, 5.65; and N, 2.09.

EXAMPLE 3 Synthesis of Compound 21

Compound 21(23.40g) was synthesized using the same method as in Synthesis example 1 except that c-1 was replaced with an equal mole of c-21, and the purity of the solid was ≧ 99.6% by HPLC. Quality of food Spectrum m/z: 799.4195 (theoretical value: 799.4178). Theoretical element content (%) C₆₁H₅₃N: c, 91.57; h, 6.68; n, 1.75. Measured elemental content (%): c, 91.50; h, 6.73; n, 1.78.

EXAMPLE 4 Synthesis of Compound 31

Compound 31(16.71g) was synthesized using the same method as in Synthesis example 1 except that c-1 was replaced with an equal mole of c-31, and the purity of the solid was ≧ 99.5% by HPLC. Mass spectrum m/z: 605.3072 (theoretical value: 605.3083). Theoretical element content (%) C₄₆H₃₉N: c, 91.20; h, 6.49; n, 2.31. Measured elemental content (%): c, 91.27; h, 6.43; n, 2.31.

EXAMPLE 5 Synthesis of Compound 33

Compound 33(21.11g) was synthesized in the same manner as in Synthesis example 1 except that c-1 was replaced with an equal mole of c-33, and the purity of the solid was ≧ 99.5% by HPLC. Mass spectrum m/z: 703.2863 (theoretical value: 703.2875). Theoretical element content (%) C₅₃H₃₇NO: c, 90.44; h, 5.30; and N, 1.99. Measured elemental content (%): c, 90.38; h, 5.35; and N, 1.97.

EXAMPLE 6 Synthesis of Compound 65

Synthesis of intermediate a-2

Under the protection of nitrogen, a three-neck flask is sequentially added with a compound E-1(13.73g,78mmol), a compound F-1(13.42g,78mmol) and a compound K₂CO₃(21.55g,156mmol)、Pd(PPh₃)₄(1.79g,1.56mmol), 600mL of a toluene/ethanol/water (3:1:1) mixed solvent was added, the mixture was stirred, and the reactant system was heated Reflux for 8 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and extracted with deionized water and toluene to obtain an organic layer, and the organic layer was washed with 400mL of deionized water for 3 times, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from toluene to obtain intermediate a-2(13.24g, yield 76%). Mass spectrum m/z: 223.1349 (theoretical value: 223.1361).

Compound 65(24.77g) was synthesized in the same manner as in Synthesis example 1 except that a-1 was replaced with an equal mole of a-2, b-1 was replaced with an equal mole of b-2, and c-1 was replaced with an equal mole of c-65, and the purity of the solid was 99.5% or more by HPLC. Mass spectrum m/z: 793.3725 (theoretical value: 793.3709). Theoretical element content (%) C₆₁H₄₇N: c, 92.27; h, 5.97; n, 1.76. Measured elemental content (%): c, 92.33; h, 5.92; n, 1.78.

EXAMPLE 7 Synthesis of Compound 138

Compound 138(17.27g) was synthesized in the same manner as in Synthesis example 1 except that c-1 was replaced with c-138 in an equimolar amount, and the purity of the solid was ≧ 99.6% by HPLC. Mass spectrum m/z: 539.2263 (theoretical value: 539.2249). Theoretical element content (%) C₄₀H₂₉NO: c, 89.02; h, 5.42; and N, 2.60. Measured elemental content (%): c, 89.07; h, 5.38; and N, 2.55.

EXAMPLE 8 Synthesis of Compound 152

Compound 152(16.97g) was synthesized in the same manner as in Synthesis example 1 except that c-1 was replaced with an equal mole of c-152, and the purity of the solid was ≧ 99.3% by HPLC. Mass spectrum m/z: 614.2736 (theoretical value: 614.2722). Theoretical element content (%) C ₄₆H₃₄N₂: c, 89.87; h, 5.57; n, 4.56. Measured elemental content (%): : c, 89.82; h, 5.53; n, 4.54.

EXAMPLE 9 Synthesis of Compound 161

Compound 161(19.58g) was synthesized in the same manner as in Synthesis example 1 except that c-1 was replaced with an equal mole of c-161, and the purity of the solid was ≧ 99.9% by HPLC. Mass spectrum m/z: 589.2419 (theoretical value: 589.2406). Theoretical element content (%) C₄₄H₃₁NO: c, 89.61; h, 5.30; and N, 2.38. Measured elemental content (%): c, 89.65; h, 5.32; and N, 2.32.

EXAMPLE 10 Synthesis of Compound 186

Compound 186(19.46g) was synthesized using the same method as in Synthesis example 1, except that c-1 was replaced with an equal mole of c-186, and the purity of the solid was ≧ 99.4% by HPLC. Mass spectrum m/z: 615.2917 (theoretical value: 615.2926). Theoretical element content (%) C₄₇H₃₇N: c, 91.67; h, 6.06; and N, 2.27. Measured elemental content (%): : c, 91.73; h, 6.02; and N, 2.24.

EXAMPLE 11 Synthesis of Compound 215

According to the same method as that of synthesis example 1, the intermediate a-3 was synthesized in the same manner as a-2 in example 6 by replacing a-1 with an equal mole of a-3 and replacing c-1 with an equal mole of b-3, thereby synthesizing compound 215(16.26g) with a solid purity of 99.8% or higher as measured by HPLC. Mass spectrum m/z: 615.2883 (theoretical value: 615.2864). Theoretical element content (%) C ₄₇H₂₉D₄N: c, 91.67; h, 6.06; and N, 2.27. Measured elemental content (%): : c, 91.60; h, 6.09; and N, 2.30.

EXAMPLE 12 Synthesis of Compound 226

To a 1L reaction flask, toluene (600mL), a-1(5.30g, 36mmol), b-4(27.60g, 72mmol), palladium acetate (0.31g, 1.4mmol), sodium tert-butoxide (13.45g, 140mmol), and tri-tert-butylphosphine (8mL in toluene) were added in that order under nitrogen. And reacted under reflux for 3 hours. After the reaction was stopped, the mixture was cooled to room temperature, filtered through celite, the filtrate was concentrated, recrystallized from methanol, filtered with suction and rinsed with methanol to give a recrystallized solid, compound 226(19.76g, 73% yield) was synthesized, and the purity of the solid was ≧ 99.4% by HPLC. Mass spectrum m/z: 751.3252 (theoretical value: 751.3239). Theoretical element content (%) C₅₈H₄₁N: c, 92.64; h, 5.50; n, 1.86. Measured elemental content (%): c, 92.70; h, 5.44; n, 1.87.

EXAMPLE 13 Synthesis of Compound 240

Using the same method as in Synthesis example 1, compound 240(21.81g) was synthesized by substituting a-1 with an equimolar amount of a-4, substituting b-1 with an equimolar amount of b-4, and substituting c-1 with an equimolar amount of c-240, and its solid purity was 99.8% or more by HPLC. Mass spectrum m/z: 767.3502 (theoretical value: 767.3490). Theoretical element content (%) C ₅₉H₃₇D₄N: c, 92.27; h, 5.91; n, 1.82. Measured elemental content (%): c, 92.33; h, 5.88; and N, 1.80.

EXAMPLE 14 Synthesis of Compound 255

According to the same method as that of synthesis example 1, intermediate a-5 was synthesized in the same manner as a-2 in example 6, by replacing a-1 with an equal mole of a-5 and replacing c-1 with an equal mole of c-255, compound 255(24.37g) was synthesized, and the purity of the solid was 99.5% or more by HPLC. Mass spectrum m/z: 827.3543 (theoretical value: 827.3552). Theoretical element content (%) C₆₃H₅₁N: c, 92.83; h, 5.48; n, 1.69. Measured elemental content (%): c, 92.87; h, 5.43; and N, 1.70.

EXAMPLE 15 Synthesis of Compound 262

Compound 262(20.90g) was synthesized in the same manner as in Synthesis example 1 except that a-1 was replaced with an equal mole of a-6 and c-1 was replaced with an equal mole of c-262, and its solid purity was determined by HPLC ≧ 99.8%. Mass spectrum m/z: 669.3044 (theoretical value: 669.3032). Theoretical element content (%) C₅₀H₃₉NO: c, 89.65; h, 5.87; and N, 2.09. Measured elemental content (%): c, 89.60; h, 5.83; and N, 2.02.

EXAMPLE 16 Synthesis of Compound 299

Compound 299(21.83g) was synthesized by using the same method as in Synthesis example 1 except that c-1 was replaced with an equal mole of c-299, and the purity of the solid was ≧ 99.6% by HPLC. Mass spectrum m/z: 699.3688 (theoretical value: 699.3679). Theoretical element content (%) C ₅₃H₂₅D₁₂N: c, 90.95; h, 7.05; n, 2.00. Measured elemental content (%): : c, 90.91; h, 7.11; n, 1.98.

EXAMPLE 17 Synthesis of Compound 331

Compound 331(17.42g) was synthesized in the same manner as in Synthesis example 1 except that b-1 was replaced with an equal mole of b-3 and c-1 was replaced with an equal mole of c-331, and the purity of the solid was 99.4% or more by HPLC. Mass spectrum m/z: 649.3537 (theoretical value: 649.3554). Theoretical element content (%) C₄₉H₂₇D₁₀N: c, 90.56; h, 7.29; and N, 2.16. Measured elemental content (%): c, 90.50; h, 7.34; and N, 2.18.

EXAMPLE 18 Synthesis of Compound 350

Using the same method as in Synthesis example 1, compound 350(21.19g) was synthesized by substituting a-1 with an equimolar a-7, b-1 with an equimolar b-5, and c-1 with an equimolar c-350, and its solid purity was ≧ 99.7% by HPLC. Mass spectrum m/z: 687.2908 (theoretical value: 687.2926). Theoretical element content (%) C₅₃H₃₇N: c, 92.54; h, 5.42; and N, 2.04. Measured elemental content (%): c, 92.58; h, 5.37; and N, 2.05.

EXAMPLE 19 Synthesis of Compound 368

Using the same method as in Synthesis example 1, compound 368(20.46g) was synthesized by substituting b-1 with an equivalent mole of b-5 and c-1 with an equivalent mole of c-368, and its solid purity was 99.3% or more by HPLC. Mass spectrum m/z: 681.3024 (theoretical value: 681.3032). Theoretical element content (%) C ₅₁H₃₉NO: c, 89.83; h, 5.77; and N, 2.05. Measured elemental content (%): c, 89.88; h, 5.73; and N, 2.02.

EXAMPLE 20 Synthesis of Compound 388

Using the same method as in Synthesis example 1, compound 388(22.13g) was synthesized by substituting a-1 with an equimolar amount of a-8, b-1 with an equimolar amount of b-5, and c-1 with an equimolar amount of c-388, and the purity of the solid was 99.4% or more by HPLC. Mass spectrum m/z: 757.3698 (theoretical value: 757.3709). Theoretical element content (%) C₅₈H₄₇N: c, 91.90; h, 6.25; n, 1.85. Measured elemental content (%): c, 91.97; h, 6.20; n, 1.82.

EXAMPLE 21 Synthesis of Compound 400

According to the same method as that of synthesis example 1, the intermediate a-9 is synthesized by the same method as that of a-2 in example 6, wherein a-1 is replaced by an equal molar amount of a-9, b-1 is replaced by an equal molar amount of b-5, and c-1 is replaced by an equal molar amount of c-400, so that compound 400(21.52g) is synthesized, and the purity of the solid is equal to or greater than 99.6% through HPLC (high performance liquid chromatography). Mass spectrum m/z: 690.3046 (theoretical value: 690.3035). Theoretical element content (%) C₅₂H₃₈N₂: c, 90.40; h, 5.54; and N, 4.05. Measured elemental content (%): c, 90.46; h, 5.50; and N, 4.03.

EXAMPLE 22 Synthesis of Compound 407

Using the same method as in Synthesis example 1, compound 407(20.90g) was synthesized by substituting a-1 with an equimolar amount of a-10, b-1 with an equimolar amount of b-5, and c-1 with an equimolar amount of c-407, and its solid purity was not less than 99.6% by HPLC. Mass spectrum m/z: 741.3406 (theoretical value: 741.3396). Theoretical element content (%) C ₅₇H₄₃N: c, 92.27; h, 5.84; n, 1.89. Measured elemental content (%): c, 92.20; h, 5.90; n, 1.92.

EXAMPLE 23 Synthesis of Compound 420

According to the same method as that of synthesis example 1, intermediate a-11 was synthesized in the same manner as a-2 in example 6, by replacing a-1 with an equal mole of a-11, replacing b-1 with an equal mole of b-3, and replacing c-1 with an equal mole of c-240, compound 420(20.37g) was synthesized, and the purity by HPLC ≧ 99.7%. Mass spectrum m/z: 697.2791 (theoretical value: 697.2770). Theoretical element content (%) C₅₄H₃₅N: c, 92.94; h, 5.06; and N, 2.01. Measured elemental content (%): c, 92.99; h,5.02；N,2.00。

EXAMPLE 24 Synthesis of Compound 422

Compound 422(16.92g) was synthesized in the same manner as in Synthesis example 1 except that a-1 was replaced with an equal mole of a-7, b-1 was replaced with an equal mole of b-6, and c-1 was replaced with an equal mole of c-422, and the purity of the solid was 99.7% or more by HPLC. Mass spectrum m/z: 595.3189 (theoretical value: 595.3177). Theoretical element content (%) C₄₅H₃₃D₄N: c, 90.71; h, 6.94; and N, 2.35. Measured elemental content (%): c, 90.67; h, 6.96; and N, 2.39.

EXAMPLE 25 Synthesis of Compound 436

Using the same method as that of Synthesis example 1, intermediate a-12 was synthesized in the same manner as a-2 in example 6, replacing a-1 with an equal mole of a-12, replacing b-1 with an equal mole of b-7, replacing c-1 with an equal mole of c-436, and synthesizing compound 436(25.14g) with a purity ≧ 99.8% by HPLC. Mass spectrum m/z: 872.4163 (theoretical value: 872.4179). Theoretical element content (%) C ₆₇H₄₄D₅N: c, 92.16; h, 6.23; and N, 1.60. Measured elemental content (%): c, 92.11; h, 6.20; n, 1.58.

EXAMPLE 26 Synthesis of Compound 473

Compound 473(22.13g) was synthesized in the same manner as in Synthesis example 1, except that b-1 was replaced with an equal molar amount of b-8 and c-1 was replaced with an equal molar amount of c-473, and the purity of the solid was determined by HPLC (high Performance liquid chromatography) and was not less than 99.9%. Mass spectrum m/z: 755.2820 (theoretical value: 755.2803). Theoretical element content (%) C₅₆H₃₉And NS: c, 88.74; h, 5.19; n, 1.85. Measured elemental content(％)：C,88.70；H,5.23；N,1.83。

EXAMPLE 27 Synthesis of Compound 487

Compound 487(20.84g) was synthesized in the same manner as in Synthesis example 1 except that b-1 was replaced with an equal mole of b-9 and c-1 was replaced with an equal mole of c-487, and its solid purity by HPLC (high performance liquid chromatography) was ≧ 99.8%. Mass spectrum m/z: 713.3097 (theoretical value: 713.3083). Theoretical element content (%) C₅₅H₃₉N: c, 92.53; h, 5.51; and N, 1.96. Measured elemental content (%): c, 92.49; h, 5.49; and N, 2.03.

EXAMPLE 28 Synthesis of Compound 505

Compound 505(24.14g) was synthesized in the same manner as in Synthesis example 1 except that a-1 was replaced with an equal mole of a-13 and c-1 was replaced with an equal mole of c-240, and its solid purity was determined by HPLC, ≧ 99.6%. Mass spectrum m/z: 763.3227 (theoretical value: 763.3239). Theoretical element content (%) C ₅₉H₄₁N: c, 92.76; h, 5.41; n, 1.83. Measured elemental content (%): c, 92.80; h, 5.40; n, 1.78.

EXAMPLE 29 Synthesis of Compound 517

Compound 517(23.15g) was synthesized by the same method as in Synthesis example 1, except that c-1 was replaced with an equal mole of c-517, and the purity of the solid was ≧ 99.5% by HPLC. Mass spectrum m/z: 566.2369 (theoretical value: 566.2358). Theoretical element content (%) C₄₁H₃₀N₂O: c, 86.90; h, 5.34; and N, 4.94. Measured elemental content (%): c, 86.93; h, 5.31; and N, 4.97.

EXAMPLE 30 Synthesis of Compound 520

According to the same method as that of synthesis example 1, the intermediate a-14 is synthesized by the same method as that of a-2 in example 6, wherein a-1 is replaced by an equal molar amount of a-14, b-1 is replaced by an equal molar amount of b-10, and c-1 is replaced by an equal molar amount of c-517, so that the compound 520(19.47g) is synthesized, and the purity of the solid is equal to or greater than 99.7% by HPLC. Mass spectrum m/z: 666.2689 (theoretical value: 666.2671). Theoretical element content (%) C₄₉H₃₄N₂O: c, 88.26; h, 5.14; and N, 4.20. Measured elemental content (%): c, 88.29; h, 5.13; n, 4.22.

EXAMPLE 31 Synthesis of Compound 521

Using the same method as in Synthesis example 1, compound 521(19.61g) was synthesized by substituting a-1 with an equimolar amount of a-8, b-1 with an equimolar amount of b-5, and c-1 with an equimolar amount of c-521, and its solid purity was not less than 99.7% by HPLC. Mass spectrum m/z: 604.2889 (theoretical value: 604.2878). Theoretical element content (%) C ₄₅H₃₆N₂: c, 89.37; h, 6.00; and N, 4.63. Measured elemental content (%): c, 89.41; h, 5.99; and N, 4.61.

EXAMPLE 32 Synthesis of Compound 542

Compound 542(19.83g) was synthesized in the same manner as in Synthesis example 1 except that a-1 was replaced with an equal mole of a-15 and c-1 was replaced with an equal mole of c-240, and its solid purity was determined by HPLC ≧ 99.8%. Mass spectrum m/z: 685.2786 (theoretical value: 685.2770). Theoretical element content (%) C₅₃H₃₅N: c, 92.81; h, 5.14; and N, 2.04. Measured elemental content (%): c, 92.84; h, 5.12; and N, 2.03.

EXAMPLE 33 Synthesis of Compound 548

Compound 548(24.34g) was synthesized in the same manner as in Synthesis example 1 except that a-1 was replaced with an equal mole of a-14 and c-1 was replaced with an equal mole of c-548, and its solid purity was measured by HPLC, ≧ 99.7%. Mass spectrum m/z: 791.3566 (theoretical value: 791.3552). Theoretical element content (%) C₆₁H₄₅N: c, 92.50; h, 5.73; n, 1.77. Measured elemental content (%): c, 92.55; h, 5.70; n, 1.74.

EXAMPLE 34 Synthesis of Compound 569

Using the same method as in Synthesis example 1, compound 569(23.16g) was synthesized by substituting a-1 with an equivalent mole of a-2 and c-1 with an equivalent mole of c-569, and its solid purity by HPLC was ≧ 99.5%. Mass spectrum m/z: 771.3673 (theoretical value: 771.3662). Theoretical element content (%) C ₅₈H₃₇D₅N₂: c, 90.24; h, 6.14; and N, 3.63. Measured elemental content (%): c, 90.26; h, 6.11; and N, 3.65.

EXAMPLE 35 Synthesis of Compound 570

Using the same method as in Synthesis example 1, compound 570(19.99g) was synthesized by substituting a-1 with an equimolar amount of a-15, b-1 with an equimolar amount of b-5, and c-1 with an equimolar amount of c-570, and having a solid purity of 99.4% or more by HPLC. Mass spectrum m/z: 640.2865 (theoretical value: 640.2878). Theoretical element content (%) C₄₈H₃₆N₂: c, 89.97; h, 5.66; n, 4.37. Measured elemental content (%): c, 90.00; h, 5.67; n, 4.32.

EXAMPLE 36 Synthesis of Compound 572

Compound 572(20.11g) was synthesized in the same manner as in Synthesis example 1, except that a-1 was replaced with an equal mole of a-5, b-1 was replaced with an equal mole of b-5, and c-1 was replaced with an equal mole of c-572, and the solid purity was ≧ 99.6% by HPLC. Mass spectrum m/z: 669.3408 (theoretical value: 669.3396). Theoretical element content (%) C₅₁H₄₃N₂: c, 91.44; h, 6.47; and N, 2.09. Measured elemental content (%): c, 91.48; h, 6.42; n, 2.11.

Green organic light emitting device (first hole transport layer)

Comparative examples 1-2 device preparation examples:

comparative example 1: the organic light-emitting device is prepared by a vacuum thermal evaporation method. The experimental steps are as follows: and (3) putting the ITO substrate into distilled water for cleaning for 3 times, ultrasonically cleaning for 15 minutes, after the cleaning of the distilled water is finished, ultrasonically cleaning solvents such as isopropanol, acetone, methanol and the like in sequence, drying at 120 ℃, and conveying to an evaporation plating machine.

Evaporating a hole injection layer CuPc/20nm, a hole transport layer HT-1/80nm and main bodies H-4 and H-14 on the prepared ITO transparent electrode in a layer-by-layer vacuum evaporation mode: GD-1 (47%: 47%: 6% mixed) mixed/28 nm was doped, then the electron transport layer BPhen/25nm, the electron injection layer LiF/1nm, the cathode Al/130nm were evaporated. And the device was sealed in a glove box, thereby preparing an organic light emitting device. After the organic light-emitting device is manufactured according to the steps, the photoelectric property of the device is measured, and the molecular structural formula of the related material is as follows:

comparative example 2: the hole transport layer material HT-1 in comparative example 1 was replaced with HT-2, and an organic light emitting device of comparative example 2 was fabricated in the same manner as in comparative example 1.

Comparative example 3: the hole transport layer material HT-1 in comparative example 1 was changed to HT-3, and an organic light emitting device of comparative example 3 was fabricated in the same manner as in comparative example 1.

[ examples 1 to 22]

Examples 1 to 22: the hole transport layer material HT-1 of the organic light emitting device was sequentially changed to the compounds 4, 9, 21, 31, 65, 138, 152, 186, 255, 331, 388, 407, 420, 422, 505, 520, 521, 526, 548, 560, 569, 570 of the present invention, and the other steps were the same as in comparative example 1.

The test software, computer, K2400 digital source 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 of the organic light emitting device. The lifetime was measured using the M6000 OLED lifetime test system from McScience. The environment of the test is atmospheric environment, and the temperature is room temperature. The results of the light emission characteristic test of the obtained organic light emitting device are shown in table 1. Table 1 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 1 test of light emitting characteristics of light emitting device

Note: t97 denotes a current density of 10mA/cm²In the case, the time taken for the luminance of the device to decay to 97%;

as can be seen from the results in table 1, the triarylamine compound containing a condensed ring according to the present invention, when applied to an organic light emitting device, as a first hole transport layer material, exhibits the advantage of high light emission efficiency as compared to comparative examples 1 to 3, and is a hole transport material for an organic light emitting device with good performance.

Red organic luminescent device (second hole transport layer)

Comparative example 4 device preparation example:

comparative example 4: the organic light-emitting device is prepared by a vacuum thermal evaporation method. The experimental steps are as follows: and (3) putting the ITO transparent substrate into distilled water for cleaning for 3 times, ultrasonically cleaning for 15 minutes, after the cleaning of the distilled water is finished, ultrasonically cleaning solvents such as isopropanol, acetone, methanol and the like in sequence, drying at 120 ℃, drying, and conveying to an evaporation plating machine.

A hole injection layer CuPc/18nm, a first hole transport layer HT1/80nm, a second hole transport layer HT-1/10nm, a luminescent layer (main body RH-6: RH-11: RD-1 (49%: 49%: 2% mixed))/26 nm, an electron transport layer BPhen/22nm, an electron injection layer LiF/0.5nm and a cathode Al/120nm are evaporated on an ITO transparent substrate electrode prepared in a layer-by-layer vacuum evaporation mode. And the device was sealed in a glove box, thereby preparing an organic light emitting device. After the organic light-emitting device is manufactured according to the steps, the photoelectric property of the device is measured, and the molecular structural formula of the related material is as follows:

[ examples 23 to 46]

Examples 23 to 46: the second hole transport layer material of the organic light emitting device was sequentially replaced with the compounds 4, 9, 21, 31, 33, 65, 138, 152, 161, 215, 226, 240, 255, 262, 299, 331, 350, 368, 388, 400, 436, 505, 542, and 572 of the present invention, and the other steps were the same as in comparative example 4.

The driving voltage and the luminous efficiency of the organic light emitting device were tested by combining test software, a computer, a K2400 digital source manufactured by Keithley, usa, and a PR788 spectral scanning luminance meter manufactured by Photo Research, usa, into a combined IVL test system. 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 in table 2, the triarylamine organic compound containing a condensed ring according to the present invention is applied to an organic light emitting device, especially as a second hole transport layer material, and compared with comparative example 4, the organic light emitting device has significantly improved light emitting efficiency and reduced driving voltage, and is an organic light emitting material with good performance.

Blue organic light emitting device (cover layer)

Comparative examples 5-6 device preparation examples:

comparative example 5: the organic light-emitting device is prepared by a vacuum thermal evaporation method. The experimental steps are as follows: and (3) putting the ITO-Ag-ITO substrate into distilled water for cleaning for 3 times, ultrasonically cleaning for 15 minutes, after the cleaning of the distilled water is finished, ultrasonically cleaning solvents such as isopropanol, acetone, methanol and the like in sequence, drying at 120 ℃, and conveying to an evaporation plating machine.

Evaporating a hole injection layer HIL/20nm, a hole transport layer Spiro-NPB/40nm and an evaporation main body BH-1 on the prepared ITO-Ag-ITO transparent electrode in a layer-by-layer vacuum evaporation mode: doping BD-1 (97%: 3%: mixed)/22 nm, then evaporating the electron transport layer Alq₃：Liq₃(1:1)/28nm, an electron injection layer LiF/1nm, a cathode Mg-Ag/20nm, and a vapor plating cover layer CP-1/68nm on the cathode. And the device was sealed in a glove box, thereby preparing an organic light emitting device. After the organic light-emitting device is manufactured according to the steps, the photoelectric property of the device is measured, and the molecular structural formula of the related material is as follows:

Comparative example 6: the cap material CP-1 of comparative example 5 was changed to CP-2, and an organic light emitting device of comparative example 6 was fabricated in the same manner as in comparative example 5.

[ examples 47 to 60]

Examples 47 to 60: the capping layer material CP-1 of the organic light emitting device was sequentially changed to the compounds 33, 161, 186, 226, 299, 350, 420, 473, 487, 517, 520, 548, 569, 570 of the present invention, and the other steps were the same as in comparative example 5.

The test software, computer, K2400 digital source 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 of the organic light emitting device. The lifetime was measured using the M6000 OLED lifetime test system from McScience. The environment of the test is atmospheric environment, and the temperature is room temperature. The results of the light emission characteristic test of the obtained organic light emitting device are shown in table 3. Table 3 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 3 test of light emitting characteristics of light emitting device

Note: t95 denotes a current density of 10mA/cm²In this case, the time taken for the luminance of the device to decay to 95%;

As can be seen from the results in table 3, the triarylamine compound containing a condensed ring of the present invention is applied to an organic light emitting device as a capping layer material, and compared with comparative examples 5 to 6, the light extraction efficiency can be effectively improved, and the light emitting efficiency of the organic light emitting device can be further improved, so that the capping layer material is an organic light emitting device capping layer material with 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.

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