阅读说明：本技术 一种包含稠环的化合物及其有机发光器件 (Compound containing condensed ring and organic light-emitting device thereof ) 是由 孙月 陆影 苗玉鹤 李梦茹 于 2021-09-24 设计创作，主要内容包括：本发明公开了一种包含稠环的化合物及其有机发光器件,涉及有机光电材料技术领域。将本发明包含稠环的化合物作为电子传输材料应用于有机发光器件中,该有机发光器件具有高的发光性能。具体表现在,本发明化合物具有较高的稳定性,作为电子传输材料或空穴阻挡材料应用于器件中,提高了电子在器件中的传输效率,并能将空穴有效地阻挡在发光层内,使电子和空穴在发光层中的复合几率升高,器件表现出高的发光效率和使用寿命。另外,将该化合物作为覆盖层应用于有机发光器件中,能有效抑制外光反射和消光反应,提高光取出性能,从而提高有机发光器件的发光效率和寿命。(The invention discloses a compound containing condensed rings and an organic light-emitting device thereof, and relates to the technical field of organic photoelectric materials. The compound containing a condensed ring of the present invention is applied to an organic light-emitting device having high light-emitting properties as an electron transport material. The compound has high stability, is used as an electron transport material or a hole blocking material in a device, improves the transport efficiency of electrons in the device, can effectively block holes in a light-emitting layer, increases the recombination probability of the electrons and the holes in the light-emitting layer, and has high light-emitting efficiency and long service life. In addition, the compound is used as a covering layer to be applied to an organic light-emitting device, so that external light reflection and extinction reaction can be effectively inhibited, and light extraction performance is improved, so that the light-emitting efficiency and the service life of the organic light-emitting device are improved.)

1. A compound containing condensed rings, which is characterized in that the compound has a structure shown as a general formula I,

the X is selected from O, S;

y is selected from C or N, and at least one Y is selected from N;

the R1 is selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl, the i1 is selected from 1,2 or 3, when the i1 is more than 1, a plurality of R1 are the same or different with each other, or two adjacent R1 can be connected to form a ring;

a is selected from substituted or unsubstituted C14-C18 condensed ring aryl;

b is the same as or different from A and is selected from one of substituted or unsubstituted C3-C15 naphthenic base, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl, and B is not selected from the group shown in the following,

the L0 is selected from one of single bond, substituted or unsubstituted arylene of C6-C25;

the L1-L2 are independently selected from one of single bonds, substituted or unsubstituted arylene of C6-C25 and substituted or unsubstituted heteroarylene of C2-C20.

2. The fused ring containing compound of claim 1, wherein the fused ring containing compound is selected from one of the structures shown below,

the R2 are the same or different from each other and are independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl, the i2 is selected from 1,2, 3,4,5, 6, 7, 8 or 9, the i3 is selected from 1,2, 3,4,5, 6 or 7, and the i4 is selected from 1,2, 3 or 4.

3. A compound containing fused rings according to claim 1, wherein A is selected from one of the following structures,

4. the compound containing fused rings of claim 1, wherein said compound isSelected from one of the structures shown below,

the R1 is the same or different and is independently selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, sec-butyl, pentyl, hexyl, heptyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, substituted or substituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, or adjacent two R1 can be connected to form a ring, the i5 is selected from 1,2 or 3, and the i6 is selected from 1 or 2.

5. The compound containing condensed rings according to claim 1, wherein B is selected from a substituted or unsubstituted C3-C15 cycloalkyl group, a substituted or unsubstituted C3-C20 cycloalkenyl group, or one of the following structures,

z is selected from C or N;

the E is selected from O, S, C (R4)₂And N (R5), wherein R4 and R5 are independently selected from one of substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;

the R3 are the same or different from each other and are independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted sec-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, and substituted or unsubstituted pyrazinyl, One of substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl and substituted or unsubstituted naphthyridinyl, or two adjacent R3 can be connected to form a ring, the i7 is selected from 1,2, 3,4 or 5, the i8 is selected from 1,2, 3,4,5, 6 or 7, the i9 is selected from 1,2, 3,4,5, 6, 7, 8 or 9, and the i10 is selected from 1,2, 3 or 4.

6. The compound having fused rings according to claim 1, wherein L1 to L2 are each independently selected from the group consisting of a single bond and one of the following structures,

the R6 are the same or different and are independently selected from one of hydrogen, deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, adamantyl, norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl and substituted or unsubstituted pyridyl, the i11 is selected from 1,2, 3 or 4, the i12 is selected from 1,2 or 3, and the i13 is selected from 1 or 2.

7. A compound containing fused rings according to claim 1, wherein said compound containing fused rings is selected from one of the following structures,

8. an organic electroluminescent device comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode, and the organic layer comprises the compound comprising a condensed ring according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, wherein the organic layer comprises at least one of an electron transport layer or a hole blocking layer, and the at least one of an electron transport layer or a hole blocking layer comprises the compound comprising a condensed ring according to any one of claims 1 to 7.

10. An organic electroluminescent device comprising an anode, a cathode, an organic layer, wherein the organic layer is located outside at least one of the anode or the cathode, and wherein the organic functional layer comprises a cover layer comprising a compound comprising 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 compound containing condensed rings and an organic light-emitting device thereof.

Background

The twenty-first century is an era of electronic information, namely, the so-called "3C" era, and in such an environment, electronic products full of Linglan are pervasive. Along with the more frequent contact between people and electronic products, people also put forward more and more demanding requirements on displays, such as small volume, high sensitivity, high Light Emitting efficiency, low power consumption, and the like, and an OLED (Organic Light Emitting Diode) display is a display capable of integrating a series of characteristics, and is a trend of future development of displays.

The OLED light-emitting device comprises electrode materials and organic functional materials sandwiched between different electrode materials, and various different functional materials are mutually overlapped together according to the application to form the OLED light-emitting device. The essence of light emission is the process of realizing photoelectric conversion, under the action of an external electric field, a cathode material generates electrons, an anode material generates holes, the electrons and the holes are respectively injected into a HOMO energy level of an electron transport layer and a LUMO energy level of a hole transport layer under the action of external voltage, the electrons at the HOMO energy level and the holes at the LUMO energy level continuously migrate to an organic light emitting layer due to the existence of energy range difference and are mutually compounded to form 'hole-electron' pairs, the 'hole-electron' pairs are excitons with higher energy, the excitons migrate freely and jump freely in the light emitting layer to generate photon energy from an excited state to a ground state, and different colors are shown according to the size of the energy, so that the process realizes the conversion of electric energy to light energy.

Photoelectric functional materials applied to OLED light-emitting devices can be divided into the following applications: a charge injection transport material, a luminescent material, and a light extraction material. The charge injection transport material may be further classified into an electron injection transport material, an electron blocking material, a hole injection transport material, and a hole blocking material, and the light emitting material includes a host light emitting material and a dopant material. In order to fabricate a high-performance OLED light-emitting device, various organic functional materials must have good photoelectric characteristics. As the charge transport material, it is required to have good carrier mobility, and as the host material of the light emitting layer, it is necessary to have good bipolar property, and as the light extraction material, it has functions of suppressing external light reflection, extinction reaction, and the like.

At present, research on organic light emitting devices mainly focuses on reducing driving voltage, improving light emitting efficiency, prolonging service life and the like, and in order to achieve continuous improvement of the performance of OLED devices, not only the innovation of OLED device structures and manufacturing processes but also the continuous research and innovation of OLED photoelectric functional materials are needed, so that it is necessary to develop OLED functional materials with higher performance.

Disclosure of Invention

The purpose of the invention is as follows: in view of the above problems, the present invention provides a compound including a condensed ring and an organic light emitting device thereof.

The compound containing condensed rings provided by the invention has a structure shown in a general formula I,

the X is selected from O, S;

y is selected from C or N, and at least one Y is selected from N;

the R1 is selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl, the i1 is selected from 1,2 or 3, when the i1 is more than 1, a plurality of R1 are the same or different with each other, or two adjacent R1 can be connected to form a ring;

a is selected from substituted or unsubstituted C14-C18 condensed ring aryl;

b is the same as or different from A and is selected from one of substituted or unsubstituted C3-C15 naphthenic base, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl, and B is not selected from the group shown in the following,

the L0 is selected from one of single bond, substituted or unsubstituted arylene of C6-C25;

the L1-L2 are independently selected from one of single bonds, substituted or unsubstituted arylene of C6-C25 and substituted or unsubstituted heteroarylene of C2-C20.

The invention provides an organic electroluminescent device which comprises an anode, a cathode and an organic layer, wherein the organic layer is positioned between the anode and the cathode, and the organic layer comprises the compound containing the condensed ring.

The invention also provides an organic electroluminescent device which comprises an anode, a cathode and an organic layer, wherein the organic layer is positioned on the outer side of at least one of the anode or the cathode, the organic functional layer comprises a covering layer, and the covering layer comprises the compound containing the condensed ring.

Has the advantages that: the compound containing the condensed ring provided by the invention is applied to an organic light-emitting device, and the organic light-emitting device has higher light-emitting performance. The fused ring-containing compound has high stability, is applied to devices as an electron transport material or a hole blocking material, improves the transport efficiency of electrons in the devices, can effectively block holes in a light emitting layer, increases the recombination probability of the electrons and the holes in the light emitting layer, and has high light emitting efficiency and long service life. In addition, the compound is used as a covering layer to be applied to an organic light-emitting device, so that external light reflection and extinction reaction can be effectively inhibited, and light extraction performance is improved, thereby improving the light-emitting efficiency of the organic light-emitting device.

Detailed Description

The present invention is further illustrated by the following examples, which are intended to be purely exemplary and are not intended to limit the scope of the invention, as various equivalent modifications of the invention will occur to those skilled in the art upon reading the present disclosure and fall within the scope of the appended claims.

In the present invention, the alkyl group may be linear or branched, and preferably has 1 to 40 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and most preferably 1 to 6 carbon atoms. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 3-dimethylbutyl, 2-ethylbutyl, pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylpentyl, 2-propylpentyl, hexyl, isohexyl, 1-methylhexyl, 4-methylhexyl, 5-methylhexyl, 2-ethylhexyl, heptyl, 1-methylheptyl, 2-dimethylheptyl, octyl, tert-octyl, nonyl, and the like.

In the present invention, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, more preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. Specific examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, and the like.

In the present invention, the cycloalkenyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, more preferably 3 to 20 carbon atoms. Specific examples of cycloalkenyl groups include, but are not limited to, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cyclobutadiene, cyclopentadiene, cycloheptene, 1, 3-cyclohexadiene, 1, 4-cyclohexadiene, and the like.

In the present invention, the aryl group may be a monocyclic aryl group, a polycyclic aryl group or a condensed ring aryl group, and preferably has 6 to 60 carbon atoms, more preferably 6 to 25 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Examples of aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, phenalene, triphenylene, and the like.

In the present invention, the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a fused ring heteroaryl group, and the number of carbon atoms is preferably 2 to 60, more preferably 2 to 20, particularly preferably 2 to 15, and most preferably 2 to 12. Wherein the heteroatoms include, but are not limited to, S, O, N, Si, P, B, and the like. Examples of heteroaryl groups include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furanyl, thienyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxadiazolyl, pyranyl, thiopyranyl, pyrazinyl, thiazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, indolyl, indolinyl, phthalazinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenanthrolinyl, phenothiazinyl, and the like.

In the present invention, the arylene group may be a monocyclic arylene group, a polycyclic arylene group or a condensed ring arylene group, and preferably has 6 to 60 carbon atoms, more preferably 6 to 25 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Examples of arylene groups include, but are not limited to, phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, anthracenylene, triphenylene, pyrenylene, fluorenylene, benzofluorenylene, spirobifluorenylene, benzospirobifluorenylene, and the like.

In the present invention, the heteroarylene may be a monocyclic heteroarylene, a polycyclic heteroarylene or a fused ring heteroarylene, and preferably has 2 to 60 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 15 carbon atoms, and most preferably 2 to 12 carbon atoms. Examples of arylene groups include, but are not limited to, pyridylene, pyrimidylene, triazinylene, furylene, thienylene, bipyrylene, phenylpyridyl, quinolylene, isoquinolylene, indolyl, benzothienyl, benzofuranylene, benzoxazolyl, benzimidazolylene, dibenzofuranylene, dibenzothiophenylene, carbazolyl, benzocarbazolyl, acridinylene, phenoxazinyl, and the like.

In the structures of the present invention, "+" indicates the attachment site.

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

In the present invention, "unsubstituted" in "substituted or unsubstituted" means that a hydrogen atom on a group is not replaced by other groups.

In the present invention, "substituted" in "substituted or unsubstituted" means that a hydrogen atom on a group is replaced with other group, and the substitution position is arbitrary, and when polysubstitution is performed, each group is the same or different, and adjacent substituent groups may be combined to form a ring. The substituent group includes deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, and specific examples include, but are not limited to, deuterium, halogen, cyano, amino, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, anthracenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, quinoxalinyl, quinazolinyl, dibenzofuranyl, dibenzothiophenyl, naphthoquinoxalinyl, naphthodibenzothiophenyl, naphthoquinoxalinyl, and naphthodibenzothiophenyl, A benzodibenzothienyl group, a carbazolyl group, an oxazolyl group, a benzoxazolyl group, a thiazolyl group, a benzothiazolyl group, an imidazolyl group, a benzimidazolyl group, and the like.

The ring which may be linked as described in the present invention means that two groups are linked to each other by a chemical bond and optionally subjected to aromatization as follows:

in the present invention, the rings connected to form the ring may be five-membered, six-membered or fused rings, examples including, but not limited to, benzene, naphthalene, fluorene, cyclopentane, cyclohexane acene, phenanthrene, grate, quinoline, isoquinoline or dibenzofuran, and the like.

The halogen in the invention comprises fluorine, chlorine, bromine and iodine.

The invention provides a compound containing condensed rings, which has a structure shown in a general formula I,

the X is selected from O, S;

y is selected from C or N, and at least one Y is selected from N;

the R1 is selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl, the i1 is selected from 1,2 or 3, when the i1 is more than 1, a plurality of R1 are the same or different with each other, or two adjacent R1 can be connected to form a ring;

a is selected from substituted or unsubstituted C14-C18 condensed ring aryl;

b is the same as or different from A and is selected from one of substituted or unsubstituted C3-C15 naphthenic base, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl, and B is not selected from the group shown in the following,

the L0 is selected from one of single bond, substituted or unsubstituted arylene of C6-C25;

the L1-L2 are independently selected from one of single bonds, substituted or unsubstituted arylene of C6-C25 and substituted or unsubstituted heteroarylene of C2-C20.

Preferably, the compound comprising fused rings is selected from one of the structures shown below,

preferably, the compound comprising fused rings is selected from one of the structures shown below,

the R2 are the same or different from each other and are independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl, the i2 is selected from 1,2, 3,4,5, 6, 7, 8 or 9, the i3 is selected from 1,2, 3,4,5, 6 or 7, and the i4 is selected from 1,2, 3 or 4.

Preferably, R2 is selected from one of hydrogen, deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, adamantyl, norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, and substituted or unsubstituted quinazolinyl.

Preferably, the A is selected from one of the following structures,

preferably, theSelected from one of the structures shown below,

the R1 is the same or different and is independently selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, sec-butyl, pentyl, hexyl, heptyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, substituted or substituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, or adjacent two R1 can be connected to form a ring, the i5 is selected from 1,2 or 3, and the i6 is selected from 1 or 2.

Preferably, the B is selected from a substituted or unsubstituted C3-C15 cycloalkyl, a substituted or unsubstituted C3-C20 cycloalkenyl or one of the structures shown below,

z is selected from C or N;

the E is selected from O, S, C (R4)₂And N (R5), wherein R4 and R5 are independently selected from one of substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;

the R3 are the same or different from each other and are independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted sec-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, and substituted or unsubstituted pyrazinyl, One of substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl and substituted or unsubstituted naphthyridinyl, or two adjacent R3 can be connected to form a ring, the i7 is selected from 1,2, 3,4 or 5, the i8 is selected from 1,2, 3,4,5, 6 or 7, the i9 is selected from 1,2, 3,4,5, 6, 7, 8 or 9, and the i10 is selected from 1,2, 3 or 4.

Preferably, B is selected from one of the following structures,

preferably, the L0 is selected from a single bond or one of the structures shown below,

preferably, L1 to L2 are selected from a single bond or one of the following structures,

the R6 are the same or different and are independently selected from one of hydrogen, deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, adamantyl, norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl and substituted or unsubstituted pyridyl, the i11 is selected from 1,2, 3 or 4, the i12 is selected from 1,2 or 3, and the i13 is selected from 1 or 2.

Preferably, L1 to L2 are selected from a single bond or one of the following structures,

preferably, the compound comprising fused rings is selected from one of the structures shown below,

in addition, the present invention provides an organic light emitting device comprising an anode, a cathode, and an organic layer between the anode and the cathode, the organic layer comprising the compound comprising a condensed ring according to the present invention.

Preferably, the organic layer includes at least one of an electron transport layer or a hole blocking layer, and the at least one of the electron transport layer or the hole blocking layer includes the compound including a condensed ring according to the present invention.

The invention also provides an organic light-emitting device comprising an anode, a cathode, an organic layer, wherein the organic layer is positioned on the outer side of at least one of the anode or the cathode, the organic functional layer comprises a covering layer, and the covering layer comprises the compound containing the condensed ring.

The organic functional layer in the organic light-emitting device provided by the invention comprises one or more of a covering layer, a hole injection layer, a first hole transport layer, a second hole transport layer/a light-emitting auxiliary layer/an electron blocking layer, a light-emitting layer, a hole blocking layer, a first electron transport layer, a second electron transport layer and an electron injection layer. The individual functional layers may be a single layer or multiple layers, each of which may comprise one or more materials.

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;

substrate/anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode;

substrate/anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode;

substrate/anode/hole injection layer/hole transport layer/electron blocking layer/luminescent layer/hole blocking layer/electron transport layer/electron injection layer/cathode;

substrate/anode/hole injection layer/hole transport layer/light-emitting auxiliary layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode;

substrate/anode/hole injection layer/hole transport layer/luminescent layer/hole blocking layer/second electron transport layer/first electron transport layer/electron injection layer/cathode;

substrate/anode/hole injection layer/first hole transport layer/second hole transport layer/luminescent layer/hole blocking layer/second electron transport layer/first electron transport layer/electron injection layer/cathode;

substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode/capping layer;

substrate/anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer;

substrate/anode/hole injection layer/hole transport layer/electron blocking layer/luminescent layer/hole blocking layer/electron transport layer/electron injection layer/cathode/cover layer;

substrate/anode/hole injection layer/hole transport layer/light-emitting auxiliary layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/cover layer;

the following is a description of the various layers and materials that may be involved in the above-described devices:

the substrate of the invention is used as a connection point of the organic light-emitting device and an external circuit, and is an important factor for smoothly injecting charges. Substrate materials that may be used in the present invention include, but are not limited to, glass, silicon, resin, metal foil, and the like.

The anode material has the characteristics of high conductivity, high light transmittance, high work function and the like, and the anode material which can be used In the invention comprises but is not limited to Indium Tin Oxide (ITO) zinc oxide (ZnO) and indium oxide (In)₂O₃) Indium Zinc Oxide (IZO), indium tin oxide/silver/indium tin oxide (ITO/Ag/ITO), aluminum/silver (Al/Ag)), and the like.

The hole injection material according to the present invention is a material that can reduce a hole injection barrier and increase interfacial charge injection, and the hole injection material that can be used in the present invention includes, but is not limited to, titanium dioxide (TiO)₂) Copper phthalocyanine (CuPc), N '-diphenyl-N, N' -di- [4- (N, N-diphenylamine) phenyl]Benzidine (NPNPB), N' -bis [4- (diphenylamino) phenyl]-N, N ' -di-1-naphthyl-biphenyl-4, 4' -diamine (NPB), 4' -tris [ 2-naphthylphenylamino]Triphenylamine (2T-NATA), and the like.

The hole transport material is a compound having a strong electron donating property and has an appropriate HOMO orbital level. The hole transport material that can be used in the present invention includes, but is not limited to, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine (NPB), N '-diphenyl-N, N' -bis (3-methylphenyl) -1,1 '-biphenyl-4, 4' -diamine (TPD), 4- [1- [4- [ bis (4-methylphenyl) amino ] phenyl ] cyclohexyl ] -N- (3-methylphenyl) -N- (4-methylphenyl) aniline (TAPC), and the like.

The electron blocking material has the characteristics of higher LUMO energy level, higher hole mobility and the like, and the electron blocking material which can be used in the invention comprises but is not limited to 4,4' -tris (carbazole-9-yl) triphenylamine (TCTA), N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB) and the like.

The luminescent material of the present invention should have good carrier transport property, semiconductor property, thermal stability and film forming property, and generally, organic electroluminescent materials are classified into fluorescent luminescent materials and phosphorescent luminescent materials. Fluorescent light-emitting materials that can be used in the present invention include, but are not limited to, 4' -bis (2, 2-diphenyl-ethen-1-yl) biphenyl (DPVBI), 2-tert-butyl-9, 10-bis (naphthalen-2-yl) anthracene (MADN), 3- (biphenyl-4-yl) -5- (4-tert-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ), and the like; phosphorescent light emitting materials that may be used in the present invention include, but are not limited to, tris [ 1-phenylisoquinoline-C2, N ] iridium, tris (2-phenylpyridine) iridium, bis (2-benzo [ b ] thiophen-2-yl-pyridine) (acetylacetone) iridium, and the like.

The hole blocking material provided by the invention generally has the characteristics of lower HOMO orbital energy level, wider band gap, higher oxidation potential, better stability, better film forming property, better mobility and the like. In addition to the compound comprising a condensed ring according to formula I of the present invention, the hole blocking material that may be used in the present invention includes, but is not limited to, 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBI), 4, 7-diphenyl-1, 10-phenanthroline (Bphen), bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1,1' -biphenyl-4-hydroxy) aluminum (BAlQ), etc., and preferably the compound comprising a condensed ring according to the present invention.

The electron transport material of the present invention has the effects of balancing carriers, enhancing electron injection, lowering working voltage, exciton blocking, etc., and in addition to the compound containing fused rings shown in formula I of the present invention, the electron transport material that can be used in the present invention includes, but is not limited to, 3'- [5' - [3- (3-pyridyl) phenyl ] [1,1':3',1 '-terphenyl ] -3, 3' -diyl ] bipyridine (TmPyPB), 4, 6-bis (3, 5-bis (3-pyridyl) phenylphenyl) -2-phenylpyrimidine (B3 PPM), PyBI, 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBI), 2- (4-biphenyl) -5- (4-tert-butylphenyl) -1,3, 4-oxadiazole (PBD), 3- (biphenyl-4-yl) -5- (4-tert-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ), 2,9- (dimethyl) -4, 7-biphenyl-1, 10-phenanthroline (BCP), 2- (naphthalene-2-yl) -4,7- (diphenyl) -1, 10-phenanthroline (HNBPHEN), 4 '-bis (4, 6-diphenyl-1, 3, 5-triazin-2-yl) -1,1' -biphenyl (BTB), and the like, preferably a compound comprising a fused ring according to the present invention.

The electron injection material according to the present invention is a material that assists the injection of electrons from the cathode into the organic layer, and the electron transport material that can be used in the present invention includes, but is not limited to, lithium oxide (Li)₂O), lithium boron oxide (LiBO)₂) Cesium carbonate (Cs)₂CO₃) Potassium silicate (K)₂SiO₃) Lithium fluoride (LiF), sodium fluoride (NaF), potassium fluoride (KF), cesium fluoride (CsF), rubidium fluoride (RbF), and the like.

The cathode material of the present invention primarily reduces the energy barrier for electron injection, and most effectively selects a metal and a metal alloy material with a lower work function, and the cathode material applicable to the present invention includes, but is not limited to, barium (Ba), calcium (Ca), lithium (Li), magnesium (Mg), aluminum (Al), indium (In), silver (Ag), magnesium-silver (Mg: Ag), lithium-aluminum (Li: Al), and the like.

The coating material of the present invention has a high glass transition temperature and excellent light extraction performance, and in addition to the compound having a condensed ring of the present invention represented by formula I, the coating material that can be used in the present invention includes, but is not limited to, imidazole derivatives, oxazole derivatives, thiazole derivatives, arylamine derivatives, and the like, and the compound having a condensed ring of the present invention is preferable.

The organic light-emitting device can be applied to the display field, such as mobile phones, digital cameras, notebook computers, electronic books, wearable intelligent equipment, flexible OLED indicator light boards and the like.

The present invention is illustrated in more detail by the following specific examples, but it should be understood that the present invention is not limited to these examples.

The compounds of formula I according to the invention can be prepared by chemical reactions known to the person skilled in the art, a synthetic route being illustrated below,

the Xn is the same or different and is selected from F, Cl, Br and I; the Bn is the same or different and is selected from

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

The instrument comprises the following steps: the mass spectrometer is a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer manufactured by Watts corporation, UK; the elemental analyzer was a Vario EL cube type organic elemental analyzer manufactured by Elementar corporation, Germany.

Synthesis example 1 Synthesis of Compound 2

Preparation of intermediate 2-1:

under the protection of nitrogen, a-2(120.00mmol, 39.99g), b-2(122.40mmol, 19.14g), Pd (PPh)₃)₄(2.40mmol, 2.77g) and 360mL of toluene, 120mL of ethanol were added to the reaction flask, the mixture was stirred, and 120mL of 2M K was added₂CO₃The aqueous solution was injected into the above solution by syringe and heated under reflux for 2 hours. After the reaction is finished and the temperature is reduced to room temperature, filter cakes are obtained by suction filtration and are usedThe filter cake was washed with ethanol and finally washed with toluene/ethanol ═ 5: 1 recrystallization to give intermediate 2-1(38.10g, 87% yield); the HPLC purity is more than or equal to 99.66 percent. Mass spectrum m/z: 364.1028 (theoretical value: 364.1019).

Preparation of intermediate 2-2:

intermediate 2-1(102.00mmol, 38.31g), c-2(112.20mmol, 28.49g) and KOAc (306.00mmol, 30.03g) were dissolved in DMF (840mL) and, after displacement with nitrogen, Pd (dppf) Cl was added₂(2.04mmol, 1.49g) was heated under reflux for 3 hours. After the reaction was completed, it was cooled to room temperature and 900mL of water was added, followed by extraction with dichloromethane, and the organic layer was extracted with anhydrous MgSO₄Drying, concentration, and recrystallization from ethyl acetate afforded intermediate 2-2(39.10g, 84% yield); the HPLC purity is more than or equal to 99.68 percent. Mass spectrum m/z: 456.2250 (theoretical value: 456.2261).

Preparation of intermediates 2-3:

under the protection of nitrogen, intermediate 2-2(85.00mmol38.79g), d-2(83.33mmol, 28.56g), Pd (PPh)₃)₄(1.67mmol, 1.93g) and 270mL of toluene, 90mL of ethanol were added to the reaction flask, the mixture was stirred, and then 90mL of 2M K was added₂CO₃The aqueous solution was injected into the above solution by a syringe and heated under reflux for 3 hours. After the reaction is finished and the temperature is reduced to room temperature, filtering to obtain a filter cake, washing the filter cake with ethanol, and finally, adding toluene/ethanol (20: 3 recrystallization to give intermediate 2-3(36.67g, 83% yield); the HPLC purity is more than or equal to 99.70 percent. Mass spectrum m/z: 518.0445 (theoretical value: 518.0437).

Preparation of intermediates 2 to 4:

intermediate 2-3(70.00mmol, 36.39g), c-2(77.00mmol, 19.55g) and KOAc (210.00mmol, 20.61g) were dissolved in DMF (560mL), and after nitrogen substitution, Pd (dppf) Cl was added₂(1.40mmol, 1.02g) was heated under reflux for 3.5 hours. After the reaction was completed, it was cooled to room temperature and 700mL of water was added, followed by extraction with dichloromethane, and the organic layer was extracted with anhydrous MgSO₄Drying, concentration, and recrystallization from ethyl acetate afforded intermediate 2-4(32.54g, 82% yield); the HPLC purity is more than or equal to 99.75 percent. Mass spectrum m/z: 566.2176 (theoretical value: 566.2184).

Preparation of intermediates 2 to 5:

under the protection of nitrogen, intermediate 2-4(56.10mmol, 31.80g), e-2(55.00mmol, 8.64g), Pd (dppf) Cl₂(1.10mmol, 0.80g), and 165mL of toluene, 55mL of ethanol were added to the reaction flask, the mixture was stirred, and 55mL of 2M K was added₂CO₃The aqueous solution was injected into the above solution by syringe and heated under reflux for 4 hours. After the reaction is finished and the temperature is reduced to room temperature, filtering to obtain a filter cake, washing the filter cake with ethanol, and finally, adding toluene/ethanol (10: 1 recrystallization to give intermediate 2-5(22.18g, 78% yield); the HPLC purity is more than or equal to 99.77 percent. Mass spectrum m/z: 516.1635 (theoretical value: 516.1645).

Preparation of intermediates 2 to 6:

intermediate 2-5(40.00mmol, 20.68g), c-2(44.00mmol, 11.17g) and KOAc (120.00mmol, 11.78g) were dissolved in DMF (320mL) and, after nitrogen substitution, Pd (dppf) Cl was added₂(0.80mmol, 0.59g) was heated under reflux for 5 hours. After the reaction was completed, it was cooled to room temperature and 400mL of water was added, followed by extraction with dichloromethane, and the organic layer was extracted with anhydrous MgSO₄Drying, concentration, and recrystallization from ethyl acetate afforded intermediate 2-6(18.26g, 75% yield); the HPLC purity is more than or equal to 99.82 percent. Mass spectrum m/z: 608.2878 (theoretical value: 608.2887).

Preparation of compound 2:

under the protection of nitrogen, intermediate 2-6(28.56mmol, 17.24g), f-2(28.00mmol, 4.32g), Pd₂(dba)₃(0.28mmol，0.26g)、P(t-Bu)₃(2.24mmol, 0.45g) and 70mL of tetrahydrofuran were added to the reaction flask, the mixture was stirred, and 23mL of 2M K was added₂CO₃The aqueous solution was injected into the above solution by syringe and heated under reflux for 5 hours. After the reaction is finished and the temperature is reduced to room temperature, filtering to obtain a filter cake, and finally recrystallizing the filter cake with toluene to obtain a compound 2(12.11g, yield 72%); the HPLC purity is more than or equal to 99.87 percent. Mass spectrum m/z: 600.2210 (theoretical value: 600.2202). Theoretical element content (%) C₄₄H₂₈N₂O: c, 87.97; h, 4.70; and N, 4.66. Measured elemental content (%): c, 87.98; h, 4.75; and N, 4.65.

Synthesis example 2 Synthesis of Compound 4

Compound 4(14.33g) was synthesized using the same method as that used for the synthesis of Compound 2 in Synthesis example 1, except that a-2 was replaced with an equimolar amount of a-4, b-2 was replaced with an equimolar amount of b-4, e-2 was replaced with an equimolar amount of e-4, and f-2 was replaced with an equimolar amount of f-4, and the purity of the solid was 99.86% or more by HPLC. Mass spectrum m/z: 730.2933 (theoretical value: 730.2922). Theoretical element content (%) C₅₄H₃₀D₄N₂O: c, 88.74; h, 5.24; and N, 3.83. Measured elemental content (%): c, 88.78; h, 5.26; and N, 3.81.

Synthesis example 3 Synthesis of Compound 13

The same procedure as used for the synthesis of Compound 2 of Synthesis example 1 was carried out in the same manner except that a-2 was replaced with an equal molar amount of a-13 and b-2 was replaced with an equal molar amount of b-13 to synthesize Compound 13(14.27g) with a solid purity of 99.88% or more by HPLC. Mass spectrum m/z: 727.2639 (theoretical value: 727.2624). Theoretical element content (%) C₅₃H₃₃N₃O: c, 87.46; h, 4.57; n, 5.77. Measured elemental content (%): c, 87.44; h, 4.63; and N, 5.75.

Synthesis example 4 Synthesis of Compound 20

The same procedure as used in Synthesis example 1 was repeated to synthesize Compound 2 by substituting a-2 with an equimolar amount of a-20, d-2 with an equimolar amount of d-20 and f-2 with an equimolar amount of f-20, whereby Compound 20(13.74g) was synthesized and had a purity of 99.87% or more as determined by HPLC. Mass spectrum m/z: 701.2481 (theoretical value: 701.2467). Theoretical element content (%) C₅₁H₃₁N₃O：C,87.28; h, 4.45; and N, 5.99. Measured elemental content (%): c, 87.30; h, 4.49; and N, 5.95.

Synthesis example 5 Synthesis of Compound 24

The same procedure as used for the synthesis of Compound 2 of Synthesis example 1 was carried out in the same manner except that a-2 was replaced with an equal molar amount of a-24 and f-2 was replaced with an equal molar amount of f-24 to synthesize Compound 24(14.76g) with a solid purity of 99.86% or more by HPLC. Mass spectrum m/z: 752.2837 (theoretical value: 752.2828). Theoretical element content (%) C₅₆H₃₆N₂O: c, 89.33; h, 4.82; and N, 3.72. Measured elemental content (%): c, 89.36; h, 4.80; and N, 3.75.

Synthesis example 6 Synthesis of Compound 26

Compound 26(13.47g) was synthesized in the same manner as in Synthesis example 1, except that b-2 was replaced with equimolar b-26, e-2 was replaced with equimolar e-26, and f-2 was replaced with equimolar f-26, whereby Compound 2(13.47g) was synthesized and had a solid purity of 99.86% or more by HPLC. Mass spectrum m/z: 677.2476 (theoretical value: 677.2467). Theoretical element content (%) C₄₉H₃₁N₃O: c, 86.83; h, 4.61; and N, 6.20. Measured elemental content (%): c, 86.80; h, 4.63; and N, 6.24.

Synthesis example 7 Synthesis of Compound 39

The same procedure used for the synthesis of Compound 2 of Synthesis example 1 was carried out in which a-2 was replaced with an equimolar amount of a-39, e-2 was replaced with an equimolar amount of e-39, and f-2 was replaced with an equimolar amount of f-39, to synthesize Compound 39(14.87g) with a purity of 99.87% by HPLC. Mass spectrum m-z: 758.2996 (theoretical value: 758.2984). Theoretical element content (%) C₅₄H₃₀D₄N₄O: c, 85.46; h, 5.05; and N, 7.38. Measured elemental content (%): c, 85.48; h, 5.10; and N, 7.39.

Synthesis example 8 Synthesis of Compound 42

The same procedure used for the synthesis of compound 2 of Synthesis example 1 was followed, except that a-2 was replaced with equimolar a-42, e-2 was replaced with equimolar e-42, and f-2 was replaced with equimolar f-20, to synthesize compound 42(17.24g) with a solid purity of 99.88% or more by HPLC. Mass spectrum m/z: 918.3629 (theoretical value: 918.3610). Theoretical element content (%) C₆₉H₄₆N₂O: c, 90.17; h, 5.04; and N, 3.05. Measured elemental content (%): c, 90.18; h, 5.08; and N, 3.02.

Synthesis example 9 Synthesis of Compound 48

Preparation of intermediate 48-1:

under the protection of nitrogen, a-48(91.80mmol, 27.37g), d-2(90.00mmol, 28.56g), Pd (PPh)₃)₄(1.80mmol, 2.08g) and 270mL of toluene, 90mL of ethanol were added to the reaction flask, the mixture was stirred, and then 90mL of 2M K was added₂CO₃The aqueous solution was injected into the above solution by a syringe and heated under reflux for 3 hours. After the reaction is finished and the temperature is reduced to room temperature, filtering to obtain a filter cake, washing the filter cake with ethanol, and finally, adding toluene/ethanol (20: 3 recrystallization to give intermediate 48-1(34.75g, 87% yield); the HPLC purity is more than or equal to 99.71 percent. Mass spectrum m/z: 442.0133 (theoretical value: 442.0124).

Preparation of intermediate 48-2:

intermediate 48-1(70.00mmol, 31.06g), c-2(77.00mmol, 19.55g) and KOAc (210.00mmol, 20.61g) were dissolved in DMF (560mL), purged with nitrogen, and then added with Pd (dppf) Cl₂(1.40mmol, 1.02g) was heated under reflux for 3.5 hours. After the reaction was completed, it was cooled to room temperature and 700mL of water was added, followed by extraction with dichloromethane, and the organic layer was extracted with anhydrous MgSO₄Drying, concentration, and recrystallization from ethyl acetate gave intermediate 48-2(28.17g, 82% yield); HPLC purity is more than or equal to 99.74 percent. Mass spectrum m/z: 490.1864 (theoretical value: 490.1871).

Preparation of intermediate 48-3:

intermediate 48-2(56.10mmol, 27.54g), e-48(55.00mmol, 17.78g), Pd (dppf) Cl were added under nitrogen₂(1.10mmol, 0.80g), and 165mL of toluene, 55mL of ethanol were added to the reaction flask, the mixture was stirred, and 55mL of 2M K was added₂CO₃The aqueous solution was injected into the above solution by syringe and heated under reflux for 4 hours. After the reaction is finished and the temperature is reduced to room temperature, filtering to obtain a filter cake, washing the filter cake with ethanol, and finally, adding toluene/ethanol (10: 1 to give intermediate 48-3(26.05g, 78% yield); the HPLC purity is more than or equal to 99.77 percent. Mass spectrum m/z: 606.1763 (theoretical value: 606.1750).

Preparation of intermediate 48-4:

intermediate 48-3(40.00mmol, 24.29g), c-2(44.00mmol, 11.17g) and KOAc (120.00mmol, 11.78g) were dissolved in DMF (320mL) and, after displacement with nitrogen, Pd (dppf) Cl was added₂(0.80mmol, 0.59g) was heated under reflux for 5 hours. After the reaction was completed, it was cooled to room temperature and 400mL of water was added, followed by extraction with dichloromethane, and the organic layer was extracted with anhydrous MgSO₄Drying, concentration, and recrystallization from ethyl acetate gave intermediate 48-4(20.96g, 75% yield); the HPLC purity is more than or equal to 99.82 percent. Mass spectrum m/z: 698.2981 (theoretical value: 698.2992).

Preparation of compound 48:

under the protection of nitrogen, intermediate 48-4(28.56mmol, 19.95g), f-48(28.00mmol, 9.11g), Pd₂(dba)₃(0.28mmol，0.26g)、P(t-Bu)₃(2.24mmol, 0.45g) and 70mL of tetrahydrofuran were added to the reaction flask, the mixture was stirred, and 23mL of 2M K was added₂CO₃Injecting the aqueous solution into the solution by a syringeIn the solution, the reaction was heated under reflux for 5 hours. After the reaction is finished and the temperature is reduced to room temperature, filtering to obtain a filter cake, and finally recrystallizing the filter cake with toluene to obtain a compound 48(15.55g, yield 68%); the HPLC purity is more than or equal to 99.85 percent. Mass spectrum m/z: 816.2767 (theoretical value: 816.2777). Theoretical element content (%) C₆₀H₃₆N₂O₂: c, 88.21; h, 4.44; n, 3.43. Measured elemental content (%): c, 88.27; h, 4.42; and N, 3.46.

Synthesis example 10 Synthesis of Compound 57

Compound 57(15.48g) was synthesized by the same method as that used for the synthesis of Compound 2 in Synthesis example 1 except that a-2 was replaced with an equimolar amount of a-57, b-2 was replaced with an equimolar amount of b-57, e-2 was replaced with an equimolar amount of e-57, and f-2 was replaced with an equimolar amount of f-57, and the purity by HPLC was 99.88% or more. Mass spectrum m/z: 812.3533 (theoretical value: 812.3515). Theoretical element content (%) C₅₈H₄₄N₄O: c, 85.69; h, 5.46; and N, 6.89. Measured elemental content (%): c, 85.74; h, 5.44; and N, 6.84.

Synthesis example 11 Synthesis of Compound 59

The same procedure as used for the synthesis of Compound 2 of Synthesis example 1 was carried out in which b-2 was replaced with an equivalent mole of b-26 and e-2 was replaced with an equivalent mole of e-59 to synthesize Compound 59(14.36g) having a solid purity of 99.87% or more by HPLC. Mass spectrum m/z: 730.2969 (theoretical value: 730.2984). Theoretical element content (%) C₅₄H₃₈N₂O: c, 88.74; h, 5.24; and N, 3.83. Measured elemental content (%): c, 88.77; h, 5.21; and N, 3.85.

Synthesis example 12 Synthesis of Compound 68

The same procedure used for the synthesis of compound 2 in Synthesis example 1 was carried out by substituting b-2 for equimolar b-68, e-2 for equimolar e-68 and f-2 for equimolar f-39 to synthesize compound 68(18.97g) with a solid purity of 99.90% by HPLC. Mass spectrum m/z: 1041.3733 (theoretical value: 1041.3719). Theoretical element content (%) C₇₈H₄₇N₃O: c, 89.89; h, 4.55; and N, 4.03. Measured elemental content (%): c, 89.87; h, 4.59; and N, 4.05.

Synthesis example 13 Synthesis of Compound 86

Compound 86(13.78g) was synthesized using the same method as that used for the synthesis of Compound 2 in Synthesis example 1, except that a-2 was replaced with an equimolar amount of a-86, d-2 was replaced with an equimolar amount of d-86, e-2 was replaced with an equimolar amount of e-86, and f-2 was replaced with an equimolar amount of f-86, and the purity of the solid was 99.86% or more by HPLC. Mass spectrum m/z: 693.2255 (theoretical value: 693.2239). Theoretical element content (%) C₄₉H₃₁N₃S: c, 84.82; h, 4.50; and N, 6.06. Measured elemental content (%): c, 84.86; h, 4.51; and N, 6.04.

Synthesis example 14 Synthesis of Compound 109

The same procedure used for the synthesis of Compound 2 of Synthesis example 1 was carried out in which a-2 was replaced with an equimolar amount of a-109, e-2 was replaced with an equimolar amount of e-109, f-2 was replaced with an equimolar amount of f-109, and Compound 109(15.71g) was synthesized with a solid purity of 99.88% or more by HPLC. Mass spectrum m/z: 824.3032 (theoretical value: 824.3022). Theoretical element content (%) C₅₉H₃₂D₅N₃S: c, 85.89; h, 5.13; and N, 5.09. Measured elemental content (%): c, 85.93; h, 5.18; n is added to the reaction solution to form a reaction solution,5.08。

synthesis example 15 Synthesis of Compound 124

The same procedure used for the synthesis of compound 2 in Synthesis example 1 was carried out by substituting b-2 for equimolar b-124, e-2 for equimolar e-4, and f-2 for equimolar f-124 to synthesize compound 124(16.09g), which had a purity of 99.88% or more as determined by HPLC. Mass spectrum m/z: 832.2563 (theoretical value: 832.2548). Theoretical element content (%) C₆₀H₃₆N₂And OS: c, 86.51; h, 4.36; and N, 3.36. Measured elemental content (%): c, 86.54; h, 4.32; n, 3.34.

Synthesis example 16 Synthesis of Compound 164

The same procedure as used for the synthesis of Compound 2 of Synthesis example 1 was followed, except that e-2 was replaced with equimolar e-164 and f-2 was replaced with equimolar f-164, to synthesize Compound 164(15.05g) with a solid purity of 99.87% or more by HPLC. Mass spectrum m/z: 778.2745 (theoretical value: 778.2733). Theoretical element content (%) C₅₆H₃₄N₄O: c, 88.74; h, 5.24; and N, 3.83. Measured elemental content (%): c, 88.78; h, 5.26; and N, 3.80.

Synthesis example 17 Synthesis of Compound 186

The same procedure as used for the synthesis of Compound 2 of Synthesis example 1 was carried out in the same manner except that a-2 was replaced with an equimolar amount of a-186 and f-2 was replaced with an equimolar amount of f-26 to synthesize Compound 186(10.72g) with a solid purity of 99.85% or more by HPLC. Mass spectrum m/z: 524.1903 (theoretical value: 524.1889). Theoretical element content (%) C₃₈H₂₄N₂O: c, 87.00; h, 4.61; n, 5.34. Measured elemental content (%): c, 87.05; h, 4.60; n, 5.31.

Synthesis example 18 Synthesis of Compound 192

The same procedure as used for the synthesis of Compound 2 of Synthesis example 1 was carried out in the same manner except that a-2 was replaced with an equal molar amount of a-192 and f-2 was replaced with an equal molar amount of f-192, whereby 192(13.47g) was synthesized, and the purity by HPLC analysis was 99.85% or more. Mass spectrum m/z: 677.2482 (theoretical value: 677.2467). Theoretical element content (%) C₄₉H₃₁N₃O: c, 86.83; h, 4.61; and N, 6.20. Measured elemental content (%): c, 86.87; h, 4.60; and N, 6.17.

Synthesis example 19 Synthesis of Compound 226

The same procedure used for the synthesis of Compound 2 of Synthesis example 1 was followed, except that a-2 was replaced with equimolar a-186, e-2 was replaced with equimolar e-226, f-2 was replaced with equimolar f-226, and Compound 226(13.29g) was synthesized with a solid purity of 99.86% or more by HPLC. Mass spectrum m/z: 677.2484 (theoretical value: 677.2467). Theoretical element content (%) C₄₉H₃₁N₃O: c, 86.83; h, 4.61; and N, 6.20. Measured elemental content (%): c, 86.88; h, 4.58; and N, 6.17.

Synthesis example 20 Synthesis of Compound 228

Synthesis of Compound 2 in the same manner as in Synthesis example 1, except that a-2 was replaced with equimolar a-228, b-2 was replaced with equimolar b-228, e-2 was replaced with equimolar e-4, and f-2 was replaced with equimolar f-20, the synthesis was carried outCompound 228(13.74g) has a solid purity ≧ 99.87% by HPLC. Mass spectrum m/z: 700.2530 (theoretical value: 700.2515). Theoretical element content (%) C₅₂H₃₂N₂O: c, 89.12; h, 4.60; and N, 4.00. Measured elemental content (%): c, 89.14; h, 4.63; and N, 3.98.

Synthesis example 21 Synthesis of Compound 237

The same procedure used for the synthesis of compound 48 in Synthesis example 9 was carried out by substituting a-48 with equimolar a-237, e-48 with equimolar e-237 and f-48 with equimolar f-237 to synthesize compound 237(14.29g) with a purity of 99.86% or more as determined by HPLC. Mass spectrum m/z: 728.2588 (theoretical value: 728.2576). Theoretical element content (%) C₅₂H₃₂N₄O: c, 85.69; h, 4.43; and N, 7.69. Measured elemental content (%): c, 85.71; h, 4.47; and N, 7.67.

Synthesis example 22 Synthesis of Compound 251

The same procedure used for the synthesis of Compound 2 of Synthesis example 1 was followed, except that a-2 was replaced with equimolar a-251, e-2 was replaced with equimolar e-251, and f-2 was replaced with equimolar f-251, to synthesize Compound 251(15.80g) with a solid purity of 99.88% or more by HPLC. Mass spectrum m/z: 841.3112 (theoretical value: 841.3093). Theoretical element content (%) C₆₂H₃₉N₃O: c, 88.44; h, 4.67; and N, 4.99. Measured elemental content (%): c, 88.49; h, 4.64; and N, 5.00.

Synthesis example 23 Synthesis of Compound 259

By the combination ofExample 1 the same procedure as used in the synthesis of Compound 2, substituting a-2 for equimolar a-259, e-2 for equimolar e-259 and f-2 for equimolar f-39 was used to synthesize Compound 259(14.82g) having a solid purity of 99.87% or more by HPLC. Mass spectrum m/z: 766.2999 (theoretical value: 766.2984). Theoretical element content (%) C₅₇H₃₈N₂O: c, 89.27; h, 4.99; and N, 3.65. Measured elemental content (%): c, 89.23; h, 5.04; n, 3.67.

Synthesis example 24 Synthesis of Compound 263

The same procedure as used in Synthesis example 1 was repeated to synthesize Compound 2 in which a-2 was replaced with an equimolar amount of a-263 and f-2 was replaced with an equimolar amount of f-263, whereby Compound 263(14.82g) was synthesized with a solid purity of 99.86% or more by HPLC. Mass spectrum m/z: 617.1946 (theoretical value: 617.1926). Theoretical element content (%) C₄₃H₂₇N₃S: c, 83.60; h, 4.41; and N, 6.80. Measured elemental content (%): c, 83.58; h, 4.40; and N, 6.86.

[ Synthesis example 25] Synthesis of Compound 323

The same procedure used for the synthesis of Compound 2 of Synthesis example 1 was carried out in the same manner as in Synthesis example 1, except that a-2 was replaced with equimolar a-323, e-2 was replaced with equimolar e-323, and f-2 was replaced with equimolar f-26, to synthesize Compound 323(14.29g) with a solid purity of 99.87% or more by HPLC. Mass spectrum m/z: 728.2561 (theoretical value: 728.2576). Theoretical element content (%) C₅₂H₃₂N₄O: c, 85.69; h, 4.43; and N, 7.69. Measured elemental content (%): c, 85.71; h, 4.40; and N, 7.67.

Synthesis example 26 Synthesis of Compound 334

The same procedure used for the synthesis of compound 2 in Synthesis example 1 was carried out by substituting a-2 with equimolar a-323, e-2 with equimolar e-334, and f-2 with equimolar f-20 to synthesize compound 334(14.47g) having a purity of 99.87% or more by HPLC. Mass spectrum m/z: 727.2638 (theoretical value: 727.2624). Theoretical element content (%) C₅₃H₃₃N₃O: c, 87.46; h, 4.57; n, 5.77. Measured elemental content (%): c, 87.48; h, 4.54; and N, 5.76.

[ Synthesis example 27] Synthesis of Compound 347

The same procedure used for the synthesis of Compound 2 in Synthesis example 1 was carried out in which a-2 was replaced with equimolar a-323, e-2 was replaced with equimolar e-347, and f-2 was replaced with equimolar f-39, to synthesize Compound 347(15.54g) with a solid purity of 99.88% or more by HPLC. Mass spectrum m/z: 815.2947 (theoretical value: 815.2937). Theoretical element content (%) C₆₀H₃₇N₃O: c, 88.32; h, 4.57; and N, 5.15. Measured elemental content (%): c, 88.36; h, 4.53; and N, 5.14.

Synthesis example 28 Synthesis of Compound 349

The same procedure used for the synthesis of compound 48 in Synthesis example 9 was carried out by substituting a-48 with equimolar a-349, e-48 with equimolar e-349 and f-48 with equimolar f-39 to synthesize compound 349(15.57g) having a purity of 99.88% by HPLC. Mass spectrum m/z: 817.2746 (theoretical value: 817.2729). Theoretical element content (%) C₅₉H₃₅N₃O₂: c, 86.64; h, 4.31; and N, 5.14. Measured elemental content (%): c, 86.68; h, 4.35; n, 5.11.

Synthesis example 29 Synthesis of Compound 352

The same procedure used for the synthesis of Compound 2 of Synthesis example 1 was carried out in which a-2 was replaced with an equimolar amount of a-323, e-2 was replaced with an equimolar amount of e-352, and f-2 was replaced with an equimolar amount of f-39, to synthesize 352(15.17g) having a purity of 99.87% by HPLC. Mass spectrum m/z: 784.3470 (theoretical value: 784.3454). Theoretical element content (%) C₅₈H₄₄N₂O: c, 88.74; h, 5.65; and N, 3.57. Measured elemental content (%): c, 88.77; h, 5.66; and N, 3.52.

Synthesis example 30 Synthesis of Compound 377

Compound 377(16.95g) was synthesized in the same manner as that for the synthesis of Compound 48 in Synthesis example 9 except that a-48 was replaced with an equimolar a-377, e-48 was replaced with an equimolar e-377, and f-48 was replaced with an equimolar f-377, and that the purity of the solid was 99.85% or more by HPLC. Mass spectrum m/z: 828.2584 (theoretical value: 828.2599). Theoretical element content (%) C₆₁H₃₆N₂S: c, 88.38; h, 4.38; and N, 3.38. Measured elemental content (%): c, 88.34; h, 4.39; n, 3.41.

Device example 1

And (2) putting the ITO glass substrate in distilled water for cleaning for 2 times, ultrasonically cleaning for 20 minutes, then cleaning for 2 times by distilled water, ultrasonically cleaning for 20 minutes, after the distilled water cleaning is finished, ultrasonically cleaning by using isopropyl alcohol, acetone and methanol in sequence, drying, and transferring the dried substrate into an evaporation machine. Sequentially evaporating a hole injection layer HI on the cleaned substrate, wherein the thickness of the hole injection layer HI is 65 nm; a hole transport layer HT having a thickness of 30 nm; a luminescent host material GH and a 5% doped luminescent material GD, the thickness of which is 30 nm; electron transport layer compound 2 of the present invention, 35nm thick; the thickness of the electron injection layer LiF is 1 nm; and the cathode Al is 110nm thick.

Device examples 2 to 15

According to the same method as in example 1, except for using compound 4, compound 20, compound 24, compound 42, compound 57, compound 86, compound 124, compound 164, compound 186, compound 228, compound 251, compound 323, compound 349, compound 377 as the electron transporting layer.

[ comparative examples 1 to 2]

The same procedure as in example 1 was followed except that compound a and compound B were used as the electron transport layer.

The molecular structural formula of the related material is shown as follows:

testing the luminous efficiency of the organic light-emitting device by combining test software, a computer, a K2400 digital source meter produced by Keithley of the United states and a PR788 spectral scanning luminance meter produced by Photo Research of the United states into a combined IVL test system; the lifetime of the organic light emitting device was tested using the M6000OLED lifetime test system of mccience corporation. The environment of the test is atmospheric environment, and the temperature is room temperature.

Table 1 shows the results of testing the light emitting characteristics of the organic light emitting devices prepared from the compounds prepared in the examples of the present invention and the comparative materials:

table 1 luminescence property test results of the devices

As can be seen from Table 1, the organic light emitting device prepared using the compound of the present invention as an electron transport layer has higher luminous efficiency and longer life span than those of comparative examples 1 to 3.

Device example 16

And (2) putting the ITO glass substrate in distilled water for cleaning for 2 times, ultrasonically cleaning for 20 minutes, then cleaning for 2 times by distilled water, ultrasonically cleaning for 20 minutes, after the distilled water cleaning is finished, ultrasonically cleaning by using isopropyl alcohol, acetone and methanol in sequence, drying, and transferring the dried substrate into an evaporation machine. Sequentially evaporating a hole injection layer HI on the cleaned substrate, wherein the thickness of the hole injection layer HI is 65 nm; a hole transport layer HT having a thickness of 30 nm; a luminescent host material GH and a 5% doped luminescent material GD, the thickness of which is 30 nm; hole blocking layer the compound of the present invention 13, 6nm in thickness; an electron transport layer ET with a thickness of 35 nm; the thickness of the electron injection layer LiF is 1 nm; and the cathode Al is 110nm thick.

Device examples 17 to 27

The same method as in example 16 was followed, except for using the compound 26, the compound 39, the compound 59, the compound 68, the compound 86, the compound 226, the compound 259, the compound 263, the compound 334, the compound 347, and the compound 349 as a hole-blocking layer.

[ comparative example 3]

The same procedure as in example 16 was followed, except that compound B was used as the hole-blocking layer.

Table 2 shows the results of the light emitting characteristic test of the organic light emitting devices prepared by the compounds prepared in the examples of the present invention and the comparative materials:

table 2 luminescence property test results of the devices

As can be seen from table 2, the compound of the present invention, introduced into an organic light emitting device as a hole transport layer, exhibits advantages of high luminous efficiency and lifetime compared to comparative examples, and is an organic light emitting material with good performance.

Device example 28

The ITO/Ag/ITO substrate is placed in distilled water to be cleaned for 2 times, the ITO glass substrate is placed in distilled water to be cleaned for 2 times, ultrasonic cleaning is carried out for 20 minutes, then the ITO/Ag/ITO substrate is cleaned for 2 times, the ITO glass substrate is cleaned for 20 minutes, then the ITO glass substrate is cleaned for 2 times by distilled water, ultrasonic cleaning is carried out for 20 minutes, after the distilled water cleaning is finished, the ITO/Ag/ITO substrate is cleaned by ultrasonic cleaning sequentially by using isopropyl acetone, acetone and methanol and then dried, and the dried substrate is transferred to an evaporation plating machine. Sequentially evaporating a hole injection layer HI on the cleaned substrate, wherein the thickness of the hole injection layer HI is 65 nm; a hole transport layer HT having a thickness of 30 nm; a luminescent host material GH and a 5% doped luminescent material GD, the thickness of which is 30 nm; an electron transport layer ET with a thickness of 35 nm; the thickness of the electron injection layer LiF is 0.5 nm; cathode Mg/Ag with thickness of 15 nm; capping layer compound 2, 60nm thick.

Device examples 29 to 37

According to the same method as in example 28 except for using compound 26, compound 48, compound 109, compound 192, compound 237, compound 251, compound 263, compound 352, compound 377 as the overcoat layer.

[ comparative example 4]

According to the same method as in example 28 except for using compound C as a covering layer.

Table 3 shows the results of the light emitting characteristic test of the organic light emitting devices prepared by the compounds prepared in the examples of the present invention and the comparative materials:

table 3 luminescence property test results of the device

As can be seen from table 3, when the compound of the present invention is applied to an organic light emitting device as a capping layer, the light emitting efficiency of the device is significantly improved at the same current density; at the same time, devices made using the compounds of the present invention have longer lifetimes.

The invention has been described in detail, but is not limited thereto, and it is intended that the invention be covered by the following claims, and that the invention be interpreted as broadly as possible, without departing from the spirit and scope of the appended claims.