CN114195794A - Light-emitting layer materials, organic electroluminescent devices and electronic equipment - Google Patents
Light-emitting layer materials, organic electroluminescent devices and electronic equipment Download PDFInfo
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- CN114195794A CN114195794A CN202111359241.1A CN202111359241A CN114195794A CN 114195794 A CN114195794 A CN 114195794A CN 202111359241 A CN202111359241 A CN 202111359241A CN 114195794 A CN114195794 A CN 114195794A
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- 230000009897 systematic effect Effects 0.000 description 1
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
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- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses a luminescent layer material, an organic electroluminescent device and electronic equipment, and relates to the technical field of organic luminescent materials, wherein the luminescent layer material comprises a first compound, the first compound is an indolocarbazole luminescent compound, the structural general formula of the indolocarbazole luminescent compound is shown in a structural formula (1), the indolocarbazole luminescent compound has excellent performances of high fluorescence quantum yield and narrow emission spectrum, so that the luminescent efficiency of the compound in the organic electroluminescent device is improved, and when the luminescent layer material is used for a luminescent layer of the organic electroluminescent device, the external quantum efficiency of the compound in the organic electroluminescent device is favorably improved, and the photoelectric performance requirement of a commercial organic electroluminescent device is met.
Description
Technical Field
The invention relates to the technical field of organic light-emitting materials, in particular to a light-emitting layer material, an organic electroluminescent device and electronic equipment.
Background
Organic light-emitting diodes (OLEDs) have made great progress over thirty years and have been widely used in small and medium-sized display products such as smart phones, wearable devices, and vehicle displays. In the OLED industry chain, organic light emitting materials have always played a crucial role, and are one of the most technically challenging areas.
At present, pyrene, stilbene and derivatives composed of the above groups are mainly used as luminescent cores, and by matching appropriate aromatic amine to modify electrical units, the charge transfer state and luminescent color of molecules are regulated, and a series of efficient new blue fluorescent materials are designed (see U.S. patent,1992, US 51629, appl.phys.lett.,1999,75,4055, chem.sci.,2016,7,4044, org.electron, 2019,70,1, and appl.mater.inter, 2017,9,26268 for details). However, when pyrene or stilbene is used as a dopant in the light-emitting layer, there is a problem that a significant shift in chromaticity coordinates is caused by a significant vibrational spectrum fine structure and accumulation between molecules. Thus, a red shift of the electroluminescence spectrum and a significant spectrum broadening effect are easily exhibited in the organic electroluminescence device. On the other hand, although conventional indolocarbazole derivatives have a rigid molecular skeleton, narrow emission spectrum characteristics are easily achieved (see adv. However, the fluorescence quantum yield of the material is only 50-60%, so that the efficiency of the prepared light-emitting device is limited (see chem.Eng.J.,2020,395,125125).
Disclosure of Invention
The invention mainly aims to provide a luminescent layer material, an organic electroluminescent device and electronic equipment, and aims to provide a luminescent layer material which is formed by an indolocarbazole derivative containing nitrogen atoms and has high efficiency and narrow emission spectrum, and the material is applied to the preparation of the organic electroluminescent device.
In order to achieve the above object, the present invention provides a light emitting layer material, including a first compound, wherein the structural general formula of the first compound is shown in structural formula (1):
wherein the ring-forming atoms bonded to the ring a and the ring b are at least one selected from carbon atoms, nitrogen atoms, oxygen atoms, silicon atoms, boron atoms, sulfur atoms and selenium atoms, R0、R1、R2、R3、R6、R7、R8、R9、R10、R13、R14、R15Each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, -N (R101) (R102), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms, r0、R1、R2、R3、R6、R7、R8、R9、R10、R13、R14、R15Are not bonded or are bonded to each other to form a further groupThe ring structure of step;
R101and R102Each independently is any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms.
The invention further provides an organic electroluminescent device, which comprises a substrate, an anode layer, an organic light-emitting functional layer and a cathode layer which are sequentially stacked from bottom to top, wherein the organic light-emitting functional layer comprises a hole injection layer, a hole transport layer, an electron injection layer and a light-emitting layer which are sequentially stacked from bottom to top, the light-emitting layer is positioned between the hole transport layer and the electron transport layer, the hole transport layer consists of a first hole transport layer and/or a second hole transport layer, the electron transport layer consists of a first electron transport layer and/or a second electron transport layer, and the material of the light-emitting layer comprises the light-emitting layer material.
The invention further proposes an electronic device comprising an organic electroluminescent device as described above.
According to the technical scheme provided by the invention, a luminescent layer material is provided, ring formation modification is introduced on an indolocarbazole molecular skeleton containing nitrogen atoms, so that the inhibition of the vibration of the indolocarbazole molecular skeleton is facilitated, and the narrow emission spectrum characteristic is easy to realize; on the other hand, the rigid ring-forming modification further inhibits non-radiative vibration, so that the fluorescence quantum yield of the indolocarbazole compound is easily improved, and the luminous efficiency of the compound in an organic electroluminescent device is improved. In addition, a donor or an acceptor unit is further connected to a substituent site of the indolocarbazole compound for regulating and controlling the energy level band gap and the light-emitting color of the compound, so that the indolocarbazole compound realizes blue light with a narrow emission spectrum. Meanwhile, the steric hindrance of the donor or acceptor unit can solve the problem of pi conjugated accumulation of the indolocarbazole molecular skeleton, avoid exciton quenching caused by accumulation, and facilitate improvement of the luminous efficiency of the compound in the organic electroluminescent device, so that the compound can meet the photoelectric performance requirement of the commercial organic electroluminescent device.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other related drawings can be obtained according to the drawings without creative efforts.
Fig. 1 is a structural diagram of a first compound of a light-emitting layer material provided by the present invention;
FIG. 2 is a schematic structural diagram of an embodiment of an organic electroluminescent device provided by the present invention;
FIG. 3 is a photoluminescence spectrum of a light-emitting layer of example 27 of the present invention;
FIG. 4 is a photoluminescence spectrum of a light-emitting layer of example 28 of the present invention.
The reference numbers illustrate:
the implementation, functional features and advantages of the objects of the present invention will be further explained with reference to the accompanying drawings.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially. In addition, the meaning of "and/or" appearing throughout includes three juxtapositions, exemplified by "A and/or B" including either A or B or both A and B. In addition, technical solutions between various embodiments may be combined with each other, but must be realized by a person skilled in the art, and when the technical solutions are contradictory or cannot be realized, such a combination should not be considered to exist, and is not within the protection scope of the present invention. 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 protection scope of the present invention.
The invention provides a luminescent layer material, and aims to provide a luminescent layer material which is formed by an indolocarbazole derivative containing a nitrogen atom and has high performance and a narrow emission spectrum, and the material is applied to the preparation of an organic electroluminescent device. Specifically, the light emitting layer material includes a first compound, and referring to fig. 1, the structural general formula of the first compound is shown in structural formula (1):
wherein the ring-forming atoms of the ring a and the ring b are selected from ring structures having at least 3 atoms and composed of at least one of carbon atoms, nitrogen atoms, oxygen atoms, silicon atoms, boron atoms, sulfur atoms and selenium atoms, the ring structures having 3 or more atoms are not formed, and R of the ring structures having 3 or more atoms is not formed0、R1、R2、R3、R6、R7、R8、R9、R10、R13、R14、R15Each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, and a substituted or unsubstituted alkyl groupSubstituted aryloxy group having 6 to 50 ring-forming carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 ring-forming carbon atoms, -N (R)101)(R102) Any one of substituted or unsubstituted aryl with 6-50 ring-forming carbon atoms and substituted or unsubstituted heteroaryl with 5-50 ring-forming carbon atoms; r101And R102Each independently represents any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms, and these substituents are not bonded or bonded to each other to form a further ring structure, and the number of ring atoms of 3 or more atoms does not include the number of atoms of the substituents.
The luminescent layer material provided by the invention introduces ring-forming modification on the molecular skeleton of the indolocarbazole containing nitrogen atoms. On one hand, the method is beneficial to inhibiting the vibration of the indolocarbazole molecular skeleton and is easy to realize the narrow emission spectrum characteristic; on the other hand, the rigid ring-forming modification further inhibits non-radiative vibration, so that the fluorescence quantum yield of the indolocarbazole compound is easily improved, and the luminous efficiency of the compound in an organic electroluminescent device is improved. In addition, a donor or an acceptor unit is further connected to a substituent site of the indolocarbazole compound for regulating and controlling the energy level band gap and the light-emitting color of the compound, so that the indolocarbazole compound realizes blue light with a narrow emission spectrum. Meanwhile, the steric hindrance of the donor or acceptor unit can solve the problem of pi conjugated accumulation of the indolocarbazole molecular skeleton, avoid exciton quenching caused by accumulation, facilitate improvement of the luminous efficiency of the compound in an organic electroluminescent device, and meet the photoelectric performance requirement of a commercial organic electroluminescent device.
It is understood that the group-N (R)101)(R102) In which N represents a nitrogen atom, R101、R102Representing two radicals attached to the nitrogen atom, e.g. the radical-N (R)101)(R102) is-NH2When R is101、R102Each represents a hydrogen atomHerein analogous, e.g. C (R)41)(R42) Wherein C represents a carbon atom, R41、R42Each represents two groups attached to a carbon atom, and the description thereof is omitted.
Preferably, in the present embodiment, ring a and ring b are each independently selected from any one of structural formulae (2) to (9):
wherein each pair of 1 and 2,3 and 4, 5 and 6,7 and 8, 9 and 10, 11 and 12, 13 and 14, and 15 and 16 represents 2 ring-forming carbon atoms to which ring a and ring b are bonded, respectively;
R21～R33each independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, amino group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, -N (R)101)(R102) Any one of substituted or unsubstituted aryl with 6-50 ring-forming carbon atoms and substituted or unsubstituted heteroaryl with 5-50 ring-forming carbon atoms; x and Y are each independently selected from C (R)41)(R42)、NR43、O、S、Se、Si，R101、R102、R41、R42、R43Each independently represents any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms, R is21～R33Wherein adjacent groups are not bonded to each other or bonded to each other to form a ringAnd (5) structure. The rings (2) to (9) are adopted for the ring a and the ring b, so that the narrow emission spectrum characteristic is realized, and the luminous efficiency is improved.
It is understood that the bonded 2 ring-forming carbon atoms such as 1 and 2 mean that the ring a and the ring b are connected to the two carbon atoms of the main ring of formula (1) to form a ring, and the description is omitted here, similarly.
In another embodiment of the present invention, preferably, ring a and ring b are each independently selected from any one of structural formulae (2), (10), (11):
wherein each pair of 1 and 2,3 and 4, and 7 and 8 represents 2 ring-forming carbon atoms to which ring a and ring b are bonded, respectively; x and Y are each independently selected from C (R)41)(R42)、NR43、O、S、Se、Si，R21、R22、R23、R24、R51、R52、R53、R54、R55、R56、R57、R58Each independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, amino group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, -N (R)101)(R102) Any one of substituted or unsubstituted aryl with 6-50 ring-forming carbon atoms and substituted or unsubstituted heteroaryl with 5-50 ring-forming carbon atoms; r41、R42、R43、R101、R102Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkane having 3 to 20 ring-forming carbon atomsAny one of a group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms, R21、R22、R23、R24、R51、R52、R53、R54、R55、R56、R57、R58Wherein adjacent groups are not bonded to each other or are bonded to each other to form a ring structure. Experiments show that the ring a and the ring b adopt any one of the rings (2), (10) and (11), thereby being beneficial to realizing narrow emission spectrum characteristics and improving luminous efficiency.
In another embodiment of the present invention, rings a and b are ring structures having 3 or more ring atoms, the ring structure being selected from any one of formulas (21) to (24),
wherein 1 and 2 represent 2 ring-forming carbon atoms to which ring a and ring b are bonded, respectively;
R61、R62、R63、R64、R65、R66、R67、R68、R69、R71、R72、R73、R74、R75、R76、R78each independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, amino group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, -N (R)101)(R102) Any of a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atomsA, R61、R62、R63、R64、R65、R66、R67、R68、R69、R71、R72、R73、R74、R75、R76、R78Wherein adjacent groups are not bonded to each other or bonded to each other to form a ring structure;
R101and R102Each independently is any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms.
The introduction of symmetrical ring a and ring b modifications in indolocarbazoles significantly enhances the conversion of the compound from S1State to S0The dipole intensity of the state radiation transition is beneficial to the improvement of the fluorescence quantum yield; on the other hand, the ring a and the ring b inhibit the molecular vibration of the indolocarbazole compound, so that the intensity of a vibration spectrum in an emission spectrum is reduced, the spread of the emission spectrum of the compound is reduced, and the organic electroluminescent device with high efficiency and narrow emission spectrum characteristics is easy to prepare.
According to the scope of the invention, the indolocarbazole compound needs to further regulate and control the energy level structure and the light-emitting band gap, so that carriers can be smoothly transmitted to the compound to be compounded to generate radiation luminescence. On the other hand, indolocarbazole has a rigid and planar molecular skeleton, exciton quenching effect of pi conjugated accumulation is easily generated, and a modification group which has steric hindrance effect and is not coplanar is introduced into a substitution site of the indolocarbazole compound to solve the problem of molecular accumulation of the indolocarbazole. Therefore, in the invention, modification groups such as phenyl and derivatives thereof, biphenyl and derivatives thereof, nitrogen-containing aromatic ring acceptor units and derivatives thereof, aromatic amine donors and derivatives thereof and the like are connected at acyclic substitution sites of the indolocarbazole shown in the formula (1).
Further, R0、R1、R2、R3、R6、R7、R8、R9、R10、R13、R14、R15Each independently selected from any one of structural formulas (30) to (37):
wherein X and Y are each independently selected from C (R)41)(R42)、NR43、O、S、Se、Si，RC、Ar1、Ar2Each independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, amino group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, -N (R)101)(R102) Any one of substituted or unsubstituted aryl with 6-50 ring-forming carbon atoms and substituted or unsubstituted heteroaryl with 5-50 ring-forming carbon atoms, wherein P1 is an integer of 0-5, P2 is an integer of 0-4, and P3 is an integer of 0-3; r41、R42、NR43、R101And R102Each independently is any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms; l is any one of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms. The substituent is selected from any one of structural formulas (30) to (37), so that the narrow emission spectrum characteristic is realized, and the luminous efficiency is improved.
In another embodiment of the present invention, preferably, R0、R1、R2、R3、R6、R7、R8、R9、R10、R13、R14、R15Each independently selected from any one of structural formulas (50) to (54):
wherein X and Y are each independently selected from C (R)41)(R42)、NR43O, S, Se, Si, in the formulae (53) and (54), RnAnd Rn+1Are bonded to each other to form a ring structure selected from the group consisting of the ring structures of formula (55) or (56), or RnAnd Rn+1Are not bonded to each other and do not form a ring, n represents an integer selected from 80 to 82 and 84 to 86, and each of pairs of 1 and 2 of formula (55) and 3 and 4 of formula (56) represents RnAnd Rn+12 ring-forming carbon atoms of the ring structure to which it is bonded;
RC、R90～R97each independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, amino group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, -N (R)101)(R102) Any one of substituted or unsubstituted aryl with 6-50 ring-forming carbon atoms and substituted or unsubstituted heteroaryl with 5-50 ring-forming carbon atoms; r41、R42、NR43、R101And R102Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkyl groupAny one of substituted or unsubstituted cycloalkyl with 3-20 ring-forming carbon atoms, substituted or unsubstituted aryl with 6-50 ring-forming carbon atoms and substituted or unsubstituted heteroaryl with 5-50 ring-forming carbon atoms, wherein P1 is an integer of 0-5, P2 is an integer of 0-4, and P4 is an integer of 0-3; l is any one of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms.
Furthermore, according to the indolocarbazole compound shown in the formula (1), a more effective ring-forming modification mode and a non-ring-forming substituent site modification mode are preferably selected so as to achieve the beneficial effects of narrow emission spectrum and improvement of molecular fluorescence quantum yield.
As a preferred embodiment of the present invention, the first compound is selected from any one of structural formulae (1-1) to (1-3):
wherein X is selected from C (R)41)(R42)、NR43、O、S、Se、Si，R0～R3、R6、R8～R10、R13～R15、R100～R107、R110～R117Each independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, amino group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, -N (R)111)(R112) Substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and substituentOr an unsubstituted heteroaryl group having 5 to 50 ring atoms, R0～R3、R6、R8～R10、R13～R15、R100～R107、R110～R117Wherein adjacent groups are not bonded to each other or bonded to each other to form a ring structure; r41、R42、R43、R111、R112Each independently is any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group with 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3-20 ring carbon atoms, a substituted or unsubstituted aryl group with 6-50 ring carbon atoms and a substituted or unsubstituted heteroaryl group with 5-50 ring carbon atoms, and when the structural formula is adopted, the luminous efficiency of the compound in an organic electroluminescent device is high.
Further, the first compound represented by the structural formula (1-2) is selected from any one of structural formulae (8-1) to (8-3):
wherein X is selected from C (R)41)(R42)、NR43、O、S、Se、Si，R0、R3、R6、R7、R13～R15、R100～R107、R170～R177Each independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, amino group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, -N (R)111)(R112) Substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and a substituentAny one of substituted or unsubstituted heteroaryl groups having 5 to 50 ring atoms; r41、R42、R43、R111、R112Each independently represents any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms, R is13～R15、R100～R107、R110～R117Wherein adjacent groups are not bonded to each other or are bonded to each other to form a ring structure. With the structural formula, the compound has high luminous efficiency in an organic electroluminescent device.
Preferably, in the structural formulae (1-1) to (1-3), (8-1) to (8-3), R0～R3、R6、R8～R10、R13～R15Each independently selected from any one of structural formulas (50) to (54):
wherein, in the formulae (53) and (54), RnAnd Rn+1Are bonded to each other to form a ring structure selected from the group consisting of the ring structures of formula (55) or (56), or RnAnd Rn+1Are not bonded to each other and do not form a ring, n represents an integer selected from 80 to 82 and 84 to 86, and each of pairs of 1 and 2 of formula (55) and 3 and 4 of formula (56) represents RnAnd Rn+12 ring-forming carbon atoms of the ring structure to which it is bonded; x and Y are each independently selected from C (R)41)(R42)、NR43、O、S、Se、Si，R80～R87Each independently selected from hydrogen atom, deuterium atom, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, -N (R)101)(R102) Any one of the group, substituted or unsubstituted aryl with 6-50 ring-forming carbon atoms and substituted or unsubstituted heteroaryl with 5-50 ring-forming carbon atoms; rC、R90～R97Each independently selected from hydrogen atomsA deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, -N (R)101)(R102) Any one of substituted or unsubstituted aryl with 6-50 ring-forming carbon atoms and substituted or unsubstituted heteroaryl with 5-50 ring-forming carbon atoms, wherein P1 is an integer of 0-5, P2 is an integer of 0-4, and P4 is an integer of 0-3; r41、R42、NR43、R101And R102Each independently is any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms; l is any one of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms.
Some specific structural formulae of the first compound of the present invention selected from any one of structural formulae (10-1) to (10-344) are given below:
the at least one material is adopted as a luminescent layer material, so that the improvement of the yield of fluorescence quantum is facilitated, the reduction of the intensity of a vibration spectrum in an emission spectrum is facilitated, the broadening of the emission spectrum of the compound is reduced, and the organic electroluminescent device with high efficiency and narrow emission spectrum characteristics is easily prepared.
The first compound can in principle be synthesized by a variety of routes, with the preferred synthetic preparation methods being as follows:
the indolocarbazole compounds are subjected to systematic photophysical performance tests, and the compounds are proved to have narrow emission spectrum characteristics and higher fluorescence quantum yield. Taking compound (10-245) as an example, the compound is dissolved in toluene (concentration of 1X 10) at room temperature-5M) was 449nm in emission peak position and 21nm in spectral half-width. The doped thin film prepared by doping the above compound in the host of (16-103) (see below) at a doping concentration of 3 wt% (as mass percentage doping concentration) was found to have a fluorescence quantum yield of 86.9%. The fluorescence quantum yield of the doped thin film of the comparative compound 3 under the same preparation conditions is 51.2%, which shows that the indolocarbazole compound disclosed by the invention has higher fluorescence quantum yield compared with the indolocarbazole compound reported in the literature. The compounds (10-245) are doped in the host (16-103) at a doping concentration of 3 wt% (mass percent doping concentration), and a corresponding electroluminescent device is prepared, wherein the electroluminescent spectrum emission peak is 455nm, and the spectrum half-peak width is 22 nm.
Further, the light-emitting layer material further includes a second compound including a compound containing a polycyclic aromatic skeleton and/or a third compound including a compound containing a polycyclic aromatic skeleton. The second compound and/or the third compound are/is adopted to dope the first compound, and the luminous efficiency of the obtained luminous layer material in the organic electroluminescent device is improved.
Preferably, the second compound comprises anthracene and derivatives thereof,
And derivatives thereof, imidazole and derivatives thereof, pyrene and derivatives thereof, fluorene and derivatives thereof; the third compound comprises anthracene and derivatives thereof,
And at least one of the derivatives thereof, imidazole and derivatives thereof, pyrene and derivatives thereof, and fluorene and derivatives thereof, so that the luminous efficiency of the luminous layer material in the organic electroluminescent device is further improved.
More preferably, the third compound includes at least one of triazine and its derivatives, pyrimidine and its derivatives, pyridine and its derivatives, boron and its derivatives, sulfuryl and its derivatives, a compound containing a skeleton of benzonitrile and its derivatives, quinoxaline and its derivatives, phosphorus and oxygen containing and its derivatives, and benzophenone and its derivatives, so that the light emitting efficiency of the light emitting layer material in the organic electroluminescent device is further improved.
Specifically, the anthracene and the derivative thereof are selected from structural formula (60):
wherein R is180～R189Independently from each other, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms in a ring, an amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms in a ring, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 carbon atoms in a ring, and-N (R is an aromatic hydrocarbon group101)(R102) A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms, -Ar or-L2-Ar, and R180～R189At least one of them is-Ar or-L2-Ar；R101And R102Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms, L2Selected from any one of substituted or unsubstituted arylene with 6-30 ring carbon atoms and substituted or unsubstituted heteroarylene with 5-30 ring carbon atoms, Ar is selected from substituted or unsubstituted arylene with 6-30 ring carbon atomsThe luminescent layer is made of any one of monocyclic group with 5-50 ring atoms, substituted or unsubstituted condensed ring group with 8-50 ring atoms and group formed by the combination of monocyclic group and condensed ring group, so that the luminous efficiency of the luminescent layer material in the organic electroluminescent device is improved.
The pyrene and its derivatives are selected from structural formula (61):
wherein R is190～R199Independently from each other, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms in a ring, an amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms in a ring, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 carbon atoms in a ring, and-N (R is an aromatic hydrocarbon group101)(R102) A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms, -Ar or-L3-Ar, and R180～R189At least one of them is-Ar or-L3-Ar；R101And R102Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms, L3The aromatic ring is selected from a single-bond substituted or unsubstituted arylene group with 6-30 ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group with 5-30 ring-forming carbon atoms, and Ar is selected from any one of a substituted or unsubstituted monocyclic group with 5-50 ring-forming carbon atoms, a substituted or unsubstituted fused ring group with 8-50 ring-forming carbon atoms and a group consisting of a combination of the monocyclic group and the fused ring group.
Specifically, the second compound and the third compound are respectively and independently selected from any one of structural formulas (16-1) to (16-190):
the at least one material is adopted as a luminescent layer material, so that the improvement of the yield of fluorescence quantum is facilitated, the reduction of the intensity of a vibration spectrum in an emission spectrum is facilitated, the broadening of the emission spectrum of the compound is reduced, and the organic electroluminescent device with high efficiency and narrow emission spectrum characteristics is easily prepared.
In an embodiment of the invention, the light emitting layer material includes a first compound with a mass fraction of 0.1% to 20% and a second compound with a mass fraction of 80% to 99.9%, the first compound is used as a dopant material, and the second compound is used as a host, which is beneficial to improving fluorescence quantum yield, reducing intensity of a vibration spectrum in an emission spectrum, and reducing spread of the emission spectrum of the compounds.
In another embodiment of the invention, the material of the light emitting layer includes a first compound with a mass fraction of 0.1% to 10%, a second compound with a mass fraction of 20% to 94.9%, and a third compound with a mass fraction of 5% to 79.9%, the first compound is used as a dopant material, and the second compound and the third compound are used as hosts, which is beneficial to improving fluorescence quantum yield, reducing intensity of a vibration spectrum in an emission spectrum, and reducing spread of the emission spectrum of the compounds.
The invention further provides an organic electroluminescent device, which comprises a substrate, an anode layer, an organic light-emitting functional layer and a cathode layer which are sequentially stacked from bottom to top, wherein the organic light-emitting functional layer comprises a hole injection layer, a hole transport layer, an electron injection layer and a light-emitting layer which are sequentially stacked from bottom to top, the light-emitting layer is positioned between the hole transport layer and the electron transport layer, the hole transport layer consists of a first hole transport layer and/or a second hole transport layer, the electron transport layer consists of a first electron transport layer and/or a second electron transport layer, and the material of the light-emitting layer 13 comprises the light-emitting layer material.
It is understood that, in the first hole transport layer and the second hole transport layer, and the first electron transport layer and the second electron transport layer of the present invention, only one layer (e.g., the first hole transport layer or the second hole transport layer) may be present in the two pairs, or both layers may be present, and when both layers are present, the first hole transport layer and the second hole transport layer are stacked in this order from the bottom to the top, and the first electron transport layer and the second electron transport layer are stacked in this order from the bottom to the top.
Referring to fig. 2, the organic electroluminescent device is composed of a substrate, an anode layer 10, an organic light emitting functional layer and a cathode layer 17, which are sequentially stacked, the organic light emitting functional layer sequentially includes any one or a combination of a hole injection layer, a first hole transport layer 11, a second hole transport layer 12, a light emitting layer 13, a first electron transport layer 14, a second electron transport layer 15 and an electron injection layer 16, and the light emitting layer 13 is located between the second hole transport layer 12 and the first electron transport layer 14. The organic electroluminescent device provided by the invention has all the beneficial effects of the luminescent layer material, and is not repeated herein.
When the light-emitting layer in the organic electroluminescent device is composed of the light-emitting layer material provided by the present invention, there is a case where a first compound containing the compound represented by the formula (1) is used as a guest material and a second compound is used as a host material in the light-emitting layer, and the second compound may be a fluorescent light-emitting type or a thermally activated delayed fluorescence mechanism material; in the case where the first compound represented by the formula (1) is used as a guest material, the second compound is used as a host material, and the third compound is used as an auxiliary host material in the light-emitting layer, the second compound may be a fluorescent light-emitting material or a thermally active delayed fluorescence mechanism material, and the third compound may be a fluorescent light-emitting material, a phosphorescent mechanism material, or a thermally active delayed fluorescence mechanism material. The first compound has the advantages of narrow emission spectrum, excellent photoelectric performance of devices and the like under the two conditions.
The anode layer mainly functions to inject holes into the hole transport layer or the light-emitting layer, and an anode layer material having a work function of 4.5eV or more is preferably used. The anode layer material is preferably selected from Indium Tin Oxide (ITO), tin oxide (NESA), Indium Gallium Zinc Oxide (IGZO), silver, and the like. The anode layer can be formed as a thin film by thermal evaporation, sputtering, or the like. It is preferable to make the light transmittance of the visible region of the anode layer greater than 80%. In addition, the sheet resistance of the anode layer is preferably 500. omega./cm-1The film thickness is preferably in the range of 10 to 200 nm.
The cathode layer mainly functions to inject electrons into the electron injection layer, the electron transport layer, or the light emitting layer, and is preferably a material having a small work function. The cathode material is not particularly limited, and is preferably selected from aluminum, magnesium, silver, a magnesium-silver alloy, a magnesium-aluminum alloy, an aluminum-lithium alloy, and the like. The cathode layer can be formed by a thin cathode layer film by a thermal deposition method, a sputtering method, or the like, similarly to the anode layer, and the thickness of the cathode layer film is preferably selected within a range of 10 to 200 nm. Further, light emission may be extracted from the cathode side as necessary.
The organic electroluminescent device of the invention preferably has an electron injection layer in the region of the interface of the cathode layer and the electron transport layer or the light-emitting layer. The electron injection layer is mainly used for promoting electrons to be injected from the cathode layer to the electron transport layer or the light emitting layer, and the light emitting brightness and the service life of the organic electroluminescent device are improved. The electron injection layer material contains a material having a work function of 3.8eV or less, and is preferably selected from Li, Cs, Ba, Yb, LiF, CsF, BaO, and the like. The electron injection layer can be formed into a thin film by thermal evaporation at a preferable evaporation rate
The thickness of the cathode layer thus produced is preferably selected within the range of 0.1 to 15 nm.
The electron transport layer of the organic electroluminescent device is an organic layer formed between the light emitting layer and the cathode layer (or the electron injection layer), mainly functions to transport electrons from the cathode to the light emitting layer, and may be composed of one layer of organic layer material, defined as a second electron transport layer; it is also possible to consist of two organic layer materials, the organic layer on the side close to the cathode layer being defined as the second electron transport layer and the organic layer on the side close to the light-emitting layer being defined as the first electron transport layer. The electron-transporting material is preferably an aromatic heterocyclic compound having 1 or more hetero atoms in the molecule, and particularly preferably a nitrogen-containing ring derivative. The nitrogen-containing ring derivative is preferably an aromatic ring having a nitrogen-containing six-membered ring or five-membered ring skeleton, or a condensed aromatic ring compound having a nitrogen-containing six-membered ring or five-membered ring skeleton.
The electron transport layer of the organic electroluminescent device of the present invention is preferably selected from the following compounds but not limited to the following structures:
the thickness of the electron transport layer is not limited, but is preferably 10 to 100 nm. When the electron transport layer of the organic electroluminescent device consists of the second electron transport layer, the film thickness of the second electron transport layer is preferably 10-100 nm; when the electron transport layer of the organic electroluminescent device is composed of the second electron transport layer and the first electron transport layer, the film thickness of the second electron transport layer is preferably 9-70 nm, and the film thickness of the first electron transport layer is preferably 1-30 nm.
The hole transport layer is an organic layer formed between the light emitting layer and the anode layer (or hole injection layer), and mainly functions to transport holes from the anode to the light emitting layer. The hole transport layer may be composed of a layer of organic material, defined as the first hole transport layer; it is also possible to consist of two layers of organic layer material, the organic layer on the side close to the anode layer being defined as the first hole transport layer and the organic layer on the side close to the light-emitting layer being defined as the second hole transport layer. As the hole transporting material used in the hole transporting layer, an aromatic amine compound, for example, an aromatic amine derivative represented by the following formula (70) is preferably used.
In the above formula (70), Ar1～Ar4The aromatic heterocyclic group is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring-forming carbon atoms (preferably 6 to 30, more preferably 6 to 20, further preferably 6 to 12), a fused aromatic hydrocarbon group having 6 to 50 ring-forming carbon atoms (preferably 6 to 30, more preferably 6 to 20, further preferably 6 to 12) which may have a substituent, an aromatic heterocyclic group having 5 to 50 ring-forming carbon atoms (preferably 5 to 30, more preferably 5 to 20, further preferably 5 to 12) which is substituted or unsubstituted, a fused aromatic heterocyclic group having 5 to 50 ring-forming carbon atoms (preferably 5 to 30, more preferably 5 to 20, further preferably 5 to 12) which is substituted or unsubstituted, or a group in which these aromatic hydrocarbon groups or aromatic hydrocarbon fused groups are bonded to an aromatic heterocyclic group or a fused aromatic heterocyclic group.
At Ar1And Ar2In between Ar3And Ar4May form a loop therebetween. L represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring-forming carbon atoms (preferably 6 to 30, more preferably 6 to 20, further preferably 6 to 12), a fused aromatic hydrocarbon group having 6 to 50 ring-forming carbon atoms (preferably 6 to 30, more preferably 6 to 20, further preferably 6 to 12) which may have a substituent, an aromatic heterocyclic group having 5 to 50 ring-forming carbon atoms (preferably 5 to 30, more preferably 5 to 20, further preferably 5 to 12) which is substituted or unsubstituted, or a fused aromatic heterocyclic group having 5 to 50 ring-forming carbon atoms (preferably 5 to 30, more preferably 5 to 20, further preferably 5 to 12) which is substituted or unsubstituted.
As the hole transporting material used for the hole transporting layer, another aromatic amine compound, for example, an aromatic amine derivative represented by the following formula (71) is preferably used.
Wherein Ar is1～Ar3And Ar in formula (70)1～Ar4The same is true.
The hole transport layer of the organic electroluminescent device of the present invention, the compounds according to formulae (70) and (71) are preferably selected from the following compounds but are not limited to the following structures:
the film thickness of the hole transport layer is not limited, but is preferably 20 to 200 nm. When the hole transport layer is composed of a first hole transport layer, the film thickness of the first hole transport layer is preferably 20 to 200 nm; when the hole transport layer is composed of a first hole transport layer and a second hole transport layer, the film thickness of the first hole transport layer is preferably 19 to 150nm, and the film thickness of the second hole transport layer is preferably 1 to 50 nm.
The organic electroluminescent device of the present invention is preferably provided with a hole injection layer in the interface region between the anode layer and the hole transport layer (or the light-emitting layer). The hole injection layer is mainly used for promoting holes to be injected into the hole transmission layer or the light emitting layer from the anode layer, so that the driving voltage of the organic electroluminescent device is reduced, and the light emitting brightness and the service life of the device are improved. The hole injection layer material is a receptor-type organic material containing a deep LUMO level, and specific examples thereof are preferably HATCN, F4-TCNQ, HI-3, and the like, and the film thickness of the hole injection layer is not particularly limited, and is preferably selected within a range of 1 to 50 nm.
The structural formulas of the hole injection layer materials HATCN, F4-TCNQ and HI-3 are as follows:
the organic electroluminescent device preferably has the main effects that the electron transport layer is doped with an n-type dopant, the hole transport layer is doped with a p-type dopant, and the n-type dopant and the p-type dopant respectively improve the transport properties of the electron transport layer and the hole transport layer and reduce the driving voltage of the organic electroluminescent device. The n-type dopant is preferably Li, Cs, Ba, Yb, CsF, BaO, Liq, Naq, Libpp, Bepq2, Bepp2, LiF, CsCO3ZnO, etc.; the p-type dopant is preferably HATCN, F4-TCNQ, HI-3, or the like. When the hole transport layer contains the p-type dopant and the hole transport material, the doping concentration of the p-type dopant is preferably 0.1% to 50.0%; when the hole transport layer contains the n-type dopant and the hole transport material, the doping concentration of the n-type dopant is preferably 1.0% to 90.0%.
Preferred n-type dopant materials for the organic electroluminescent device of the present invention, Liq, Naq, Libpp, Bepq2, Bepp2, have the following structural formulae:
the invention further provides an electronic device, which is the organic electroluminescent device. The electronic device provided by the invention has all the beneficial effects of the organic electroluminescent device, and the details are not repeated herein.
The technical solutions of the present invention are further described in detail below with reference to specific examples and drawings, it should be understood that the following examples are merely illustrative of the present invention and are not intended to limit the present invention.
EXAMPLE 1 preparation of the first Compound (10-1)
8, 8-dimethyl-5, 8-dihydroindeno [2,1-c ] carbazole (2g, 7.06mmol, 1eq), sodium hydride (NaH) (0.17g, 7.06mmol, 1eq) and 1, 5-dibromo-2, 4-difluorobenzene (1g, 3.67mmol, 0.52eq) were dispersed in 20mL of N, N' -Dimethylformamide (DMF) under a nitrogen atmosphere and reacted at 60 ℃ for 12 hours. After the reaction was completed, a large amount of water was added, extraction was performed with dichloromethane, and the organic layer was collected and dried over anhydrous magnesium sulfate. The crude product was purified by column chromatography using petroleum ether: the dichloromethane (90:10) was further purified. Intermediate 1 was obtained in a yield of 2.1g (75% yield).
Under a nitrogen atmosphere, intermediate 1(1g, 1.25mmol,1eq), palladium (II) acetate [ Pd (OAc)2](0.14g, 0.63mmol, 0.5eq), triphenylphosphine (PPh)3) A mixture of (0.2g, 0.75mmol, 0.6eq), benzyltriethylammonium chloride (0.57g, 2.5mmol, 2eq) and potassium carbonate (1.73g, 10mmol, 8eq) was dispersed in 20mL of N, N' -Dimethylacetamide (DMAC) and reacted at 140 ℃ for 12 hours. After the reaction was completed, a large amount of water was added, extraction was performed with dichloromethane, and the organic layer was collected and dried over anhydrous magnesium sulfate. The crude product was purified by column chromatography using petroleum ether: dichloromethane (90:10) was used as eluent. Obtained (10-1) as a white solid with a yield of 0.26g (33% yield).
EXAMPLE 2 preparation of first Compounds (10-17)
8H-benzofuran [2,3-c ] carbazole (1.8g, 7.06mmol, 1eq), sodium hydride (NaH) (0.17g, 7.06mmol, 1eq) and 1, 5-dibromo-2, 4-difluorobenzene (1g, 3.67mmol, 0.52eq) were dispersed in 20mL of N, N' -Dimethylformamide (DMF) under a nitrogen atmosphere and reacted at 60 ℃ for 12 hours. After the reaction was completed, a large amount of water was added, extraction was performed with dichloromethane, and the organic layer was collected and dried over anhydrous magnesium sulfate. The crude product was purified by column chromatography using petroleum ether: the dichloromethane (90:10) was further purified. Intermediate 2 was obtained in a yield of 1.8g (70% yield).
Under a nitrogen atmosphere, intermediate 2(0.9g,1.25mmol,1eq), palladium (II) acetate [ Pd (OAc)2](0.14g, 0.63mmol, 0.5eq), triphenylphosphine (PPh)3) A mixture of (0.2g, 0.75mmol, 0.6eq), benzyltriethylammonium chloride (0.57g, 2.5mmol, 2eq) and potassium carbonate (1.73g, 10mmol, 8eq) was dispersed in 20mL of N, N' -Dimethylacetamide (DMAC) and reacted at 140 ℃ for 12 hours. After the reaction was completed, a large amount of water was added, extraction was performed with dichloromethane, and the organic layer was collected and dried over anhydrous magnesium sulfate. The crude product was purified by column chromatography using petroleum ether: dichloromethane (90:10) was used as eluent. Obtained as a white solid (10-17) with a yield of 0.29g (40% yield).
EXAMPLE 3 preparation of the first Compound (10-20)
7H-Benzocarbazole (1.5g, 7.06mmol, 1eq), sodium hydride (NaH) (0.17g, 7.06mmol, 1eq) and 1, 5-dibromo-2, 4-difluorobenzene (1g, 3.67mmol, 0.52eq) were dispersed in 20mL of N, N' -Dimethylformamide (DMF) under a nitrogen atmosphere and reacted at 60 ℃ for 12 hours. After the reaction was completed, a large amount of water was added, extraction was performed with dichloromethane, and the organic layer was collected and dried over anhydrous magnesium sulfate. The crude product was purified by column chromatography using petroleum ether: the dichloromethane (90:10) was further purified. Intermediate 3 was obtained in a yield of 1.1g (60% yield).
Under nitrogen atmosphere, intermediate 3(0.8g, 1.25mmol,1eq), palladium (II) acetate [ Pd (OAc)2](0.14g, 0.63mmol, 0.5eq), triphenylphosphine (PPh)3) A mixture of (0.2g, 0.75mmol, 0.6eq), benzyltriethylammonium chloride (0.57g, 2.5mmol, 2eq) and potassium carbonate (1.73g, 10mmol, 8eq) was dispersed in 20mL of N, N-Dimethylacetamide (DMAC) and reacted at 140 ℃ for 12 hours. After the reaction was completed, a large amount of water was added, extraction was performed with dichloromethane, and the organic layer was collected and dried over anhydrous magnesium sulfate. The crude product was purified by column chromatography using petroleum ether: dichloromethane (90:10) was used as eluent. 10-20 was obtained as a white solid with a yield of 0.15g (25% yield).
EXAMPLE 4 preparation of the first Compound (10-21)
9H-carbazole-3-boronic acid pinacol ester (2g, 6.82mmol, 1eq), o-bromobenzene (1.93g, 8.19mmol, 1.2eq), palladium tetratriphenylphosphine (157mg, 0.13mmol, 0.02eq) and potassium carbonate (1.4g, 10.2mmol, 1.5eq) were dispersed in 30mL of toluene under a nitrogen atmosphere, and reacted at 100 ℃ for 12 hours. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: the dichloromethane (90:10) was further purified. Intermediate 4 was obtained in a yield of 2.0g (90% yield).
Intermediate 4(2g, 5.65mmol, 1eq), di-tert-butyl dicarbonate (1.5g, 6.78mmol, 1.2eq) and 4-dimethylaminopyridine (0.69g, 5.65mmol, 1eq) were dispersed in 30mL of Tetrahydrofuran (THF) in air and reacted at room temperature for 4 hours. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: dichloromethane (80:20) was further purified. Intermediate 5 was obtained in a yield of 2.1g (90% yield).
Under a nitrogen atmosphere, intermediate 5(2g, 4.73mmol, 1eq) was dispersed in 20mL of ultra-dry Tetrahydrofuran (THF), an n-hexane solution of n-butyllithium (1.6mol/L, 3.5mL, 1.2eq) was added dropwise at-78 deg.C, after 1 hour of reaction, benzophenone (1.3g, 7.09mmol, 1.5eq) was dissolved in 10mL of tetrahydrofuran solution and added to the system, and after completion of the addition, the reaction was returned to room temperature for 12 hours. Then adding acetic acid and hydrochloric acid for acidification, adjusting the pH value to be weakly acidic, and continuing the reaction for 4 hours. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: dichloromethane (80:20) was further purified. Intermediate 6 was obtained in a yield of 1.2g (60% yield).
Intermediate 6(2.8g, 7.06mmol, 1eq), sodium hydride (NaH) (0.17g, 7.06mmol, 1eq) and 1, 5-dibromo-2, 4-difluorobenzene (1g, 3.67mmol, 0.52eq) were dispersed in 20mL of DMF under a nitrogen atmosphere and reacted at 60 ℃ for 12 hours. After the reaction was completed, a large amount of water was added, extraction was performed with dichloromethane, and the organic layer was collected and dried over anhydrous magnesium sulfate. The crude product was purified by column chromatography using petroleum ether: the dichloromethane (90:10) was further purified. Intermediate 7 was obtained in a yield of 2.2g (60% yield).
Under a nitrogen atmosphere, intermediate 7(1.3g, 1.25mmol,1eq), palladium (II) acetate [ Pd (OAc)2](0.14g, 0.63mmol, 0.5eq), triphenylphosphine (PPh)3) A mixture of (0.2g, 0.75mmol, 0.6eq), benzyltriethylammonium chloride (0.57g, 2.5mmol, 2eq) and potassium carbonate (1.73g, 10mmol, 8eq) was dispersed in 20mL DMAC and reacted at 140 ℃ for 12 hours. After the reaction was completed, a large amount of water was added, extraction was performed with dichloromethane, and the organic layer was collected and dried over anhydrous magnesium sulfate. The crude product was purified by column chromatography using petroleum ether: dichloromethane (90:10) was used as eluent. Obtained as a white solid (10-21) with a yield of 0.33g (30% yield).
EXAMPLE 5 preparation of first Compounds (10-38)
Under a nitrogen atmosphere, compound 10-1(3g, 4.7mmol, 1eq) was dispersed in 30mL of acetonitrile, after which N-bromosuccinimide (2.1g, 11.7mmol, 2.5eq) was added in one portion and reacted at room temperature for 12 hours with exclusion of light. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: the dichloromethane (60:40) was further purified. Intermediate 8 was obtained in a yield of 3.3g (90% yield).
Intermediate 8(2.5g, 3.2mmol, 1eq), phenylboronic acid (1.1g, 9.5mmol, 3eq), tetratriphenylphosphine palladium (167mg, 0.13mmol, 0.04eq) and potassium carbonate (1.3g, 9.5mmol, 3eq) were dispersed in 30mL toluene under a nitrogen atmosphere and reacted at 100 ℃ for 12 hours. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: the dichloromethane (90:10) was further purified. The product (10-38) was obtained in a yield of 1.0g (40% yield).
EXAMPLE 6 preparation of first Compound (10-61)
Intermediate 8(2.5g, 3.2mmol, 1eq), (9, 9-dimethyl-9H-fluoren-3-yl) boronic acid (2.3g, 9.5mmol, 3eq), tetrakistriphenylphosphine palladium (167mg, 0.13mmol, 0.04eq) and potassium carbonate (1.3g, 9.5mmol, 3eq) were dispersed in 30mL toluene under a nitrogen atmosphere and reacted at 100 ℃ for 12 hours. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: dichloromethane (80:20) was further purified. The product (10-61) was obtained in a yield of 1.6g (40% yield).
EXAMPLE 7 preparation of first Compounds (10-71)
Intermediate 8(2.5g, 3.2mmol, 1eq), diphenylamine (1.6g, 9.5mmol, 3eq), cuprous iodide (25mg, 0.13mmol, 0.04eq), phenanthroline (23mg, 0.13mmol, 0.04eq) and potassium carbonate (1.3g, 9.5mmol, 3eq) were dispersed in 10mL of azomethylpyrrolidone under a nitrogen atmosphere and reacted at 180 ℃ for 16 hours. After the reaction is finished, adding water and dichloromethane for extraction, collecting an organic phase, spin-drying a solvent, and performing column chromatography on a crude product by using petroleum ether: dichloromethane (50:50) was further purified. The product (10-71) was obtained in a yield of 1.2g (40% yield).
EXAMPLE 8 synthetic preparation of the first Compound (10-90)
(9, 9-dimethyl-9H-fluoren-3-yl) amine (2.0g, 9.5mmol, 1eq), 1, 4-dimethyl-2-iodobenzene (2.6g, 11.4mmol, 1.2eq), tris (dibenzylideneacetone) dipalladium (173mg, 0.19mmol, 0.02eq), 1, 1' -bis (diphenylphosphino) ferrocene (107mg, 0.19mmol, 0.02eq) and sodium tert-butoxide (1.3g, 14.2mmol, 1.5eq) were dispersed in 20mL of toluene under a nitrogen atmosphere. The reaction was carried out at 120 ℃ for 16 hours. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: dichloromethane (50:50) was further purified. Intermediate 9 was obtained in a yield of 2.6g (90% yield).
Intermediate 8(2.5g, 3.2mmol, 1eq), intermediate 9(2.9g, 9.5mmol, 3eq), cuprous iodide (25mg, 0.13mmol, 0.04eq), phenanthroline (23mg, 0.13mmol, 0.04eq) and potassium carbonate (1.3g, 9.5mmol, 3eq) were dispersed in 10mL of azomethylpyrrolidone under a nitrogen atmosphere and reacted at 180 ℃ for 16 hours. After the reaction is finished, adding water and dichloromethane for extraction, collecting an organic phase, spin-drying a solvent, and performing column chromatography on a crude product by using petroleum ether: dichloromethane (50:50) was further purified. The product was obtained (10-90) in a yield of 0.7g (20% yield).
EXAMPLE 9 synthetic preparation of first Compounds (10-109)
Intermediate 8(2.5g, 3.2mmol, 1eq), 7H-dibenzocarbazole (2.5g, 9.5mmol, 3eq), cuprous iodide (25mg, 0.13mmol, 0.04eq), phenanthroline (23mg, 0.13mmol, 0.04eq), and potassium carbonate (1.3g, 9.5mmol, 3eq) were dispersed in 10mL of azomethylpyrrolidone under a nitrogen atmosphere and reacted at 180 ℃ for 16 hours. After the reaction is finished, adding water and dichloromethane for extraction, collecting an organic phase, spin-drying a solvent, and performing column chromatography on a crude product by using petroleum ether: dichloromethane (50:50) was further purified. The product was obtained (10-109) in a yield of 1.2g (34% yield).
EXAMPLE 10 synthetic preparation of the first Compounds (10-124)
Intermediate 8(2.5g, 3.2mmol, 1eq), 10H-spiro [ acridine-9, 9' -fluorene ] (3.1g, 9.5mmol, 3eq), cuprous iodide (25mg, 0.13mmol, 0.04eq), phenanthroline (23mg, 0.13mmol, 0.04eq) and potassium carbonate (1.3g, 9.5mmol, 3eq) were dispersed in 10mL of N-methylpyrrolidone under a nitrogen atmosphere and reacted at 180 ℃ for 16 hours. After the reaction is finished, adding water and dichloromethane for extraction, collecting an organic phase, spin-drying a solvent, and performing column chromatography on a crude product by using petroleum ether: dichloromethane (50:50) was further purified. The product was obtained (10-124) in a yield of 1.6g (40% yield).
EXAMPLE 11 synthetic preparation of the first Compounds (10-162)
Compound 10-1(3g, 4.7mmol, 1eq) was dispersed in 30mL acetonitrile under nitrogen, after which N-bromosuccinimide (0.84g, 4.68mmol, 1eq) was added in one portion and reacted at room temperature with exclusion of light for 12 hours. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: the dichloromethane (60:40) was further purified. Intermediate 10 was obtained in a yield of 2.7g (80% yield).
2-naphthylamine (1.4g, 9.5mmol, 1eq), 4-iodo-1, 1 '-biphenyl (3.2g, 11.4mmol, 1.2eq), tris (dibenzylideneacetone) dipalladium (173mg, 0.19mmol, 0.02eq), 1, 1' -bis (diphenylphosphino) ferrocene (107mg, 0.19mmol, 0.02eq) and sodium tert-butoxide (1.3g, 14.2mmol, 1.5eq) were dispersed in 20mL of toluene under a nitrogen atmosphere. The reaction was carried out at 120 ℃ for 16 hours. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: dichloromethane (50:50) was further purified. Intermediate 11 was obtained in a yield of 2.5g (90% yield).
Intermediate 10(2.3g, 3.2mmol, 1eq), 11(1.1g, 3.8mmol, 1.2eq), cuprous iodide (13mg, 0.06mmol, 0.02eq), phenanthroline (12mg, 0.06mmol, 0.02eq) and potassium carbonate (0.6g, 9.5mmol, 1.5eq) were dispersed in 10mL of azomethylpyrrolidone under a nitrogen atmosphere and reacted at 180 ℃ for 16 hours. After the reaction is finished, adding water and dichloromethane for extraction, collecting an organic phase, spin-drying a solvent, and performing column chromatography on a crude product by using petroleum ether: dichloromethane (50:50) was further purified. The product was obtained (10-162) in a yield of 1.5g (50% yield).
EXAMPLE 12 synthetic preparation of the first Compound (10-179)
4-amino-1, 1 '-biphenyl (1.6g, 9.5mmol, 1eq), 4-bromodibenzofuran (2.8g, 11.4mmol, 1.2eq), tris (dibenzylideneacetone) dipalladium (173mg, 0.19mmol, 0.02eq), 1, 1' -bis (diphenylphosphino) ferrocene (107mg, 0.19mmol, 0.02eq) and sodium tert-butoxide (1.3g, 14.2mmol, 1.5eq) were dispersed in 20mL of toluene under a nitrogen atmosphere. The reaction was carried out at 120 ℃ for 16 hours. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: dichloromethane (50:50) was further purified. Intermediate 12 was obtained in a yield of 2.8g (90% yield).
Intermediate 10(2.3g, 3.2mmol, 1eq), 12(1.2g, 3.8mmol, 1.2eq), cuprous iodide (13mg, 0.06mmol, 0.02eq), phenanthroline (12mg, 0.06mmol, 0.02eq) and potassium carbonate (0.6g, 9.5mmol, 1.5eq) were dispersed in 10mL of azomethylpyrrolidone under a nitrogen atmosphere and reacted at 180 ℃ for 16 hours. After the reaction is finished, adding water and dichloromethane for extraction, collecting an organic phase, spin-drying a solvent, and performing column chromatography on a crude product by using petroleum ether: the dichloromethane (40:60) was further purified. The product was obtained (10-179) with a yield of 1.8g (60% yield).
EXAMPLE 13 synthetic preparation of the first Compound (10-191)
5, 11-dihydro-11, 11-dimethylindeno [1,2-B ] carbazole (1.3g, 4.7mmol, 1eq) was dispersed in 30mL of acetonitrile under nitrogen, after which N-bromosuccinimide (0.84g, 4.68mmol, 1eq) was added in one portion and reacted at room temperature with exclusion of light for 12 hours. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: the dichloromethane (60:40) was further purified. Intermediate 13 was obtained in a yield of 1.5g (90% yield).
Intermediate 13(1.2g, 3.2mmol, 1eq), phenylboronic acid (0.5g, 3.8mmol, 1.2eq), palladium tetratriphenylphosphine (167mg, 0.13mmol, 0.04eq) and potassium carbonate (0.6g, 9.5mmol, 1.5eq) were dispersed in 30mL of toluene under nitrogen and reacted at 100 ℃ for 12 hours. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: dichloromethane (80:20) was further purified. Intermediate 14 was obtained in a yield of 1.0g (90% yield).
Intermediate 10(2.3g, 3.2mmol, 1eq), 14(1.4g, 3.8mmol, 1.2eq), cuprous iodide (13mg, 0.06mmol, 0.02eq), phenanthroline (12mg, 0.06mmol, 0.02eq) and potassium carbonate (0.6g, 9.5mmol, 1.5eq) were dispersed in 10mL of azomethylpyrrolidone under a nitrogen atmosphere and reacted at 180 ℃ for 16 hours. After the reaction is finished, adding water and dichloromethane for extraction, collecting an organic phase, spin-drying a solvent, and performing column chromatography on a crude product by using petroleum ether: the dichloromethane (30:70) was further purified. The product (10-191) was obtained in a yield of 1.9g (60% yield).
EXAMPLE 14 synthetic preparation of first Compounds (10-205)
Compound 10-17(2.7g, 4.7mmol, 1eq) was dispersed in 30mL acetonitrile under nitrogen, after which N-bromosuccinimide (2.1g, 11.7mmol, 2.5eq) was added in one portion and reacted at room temperature with exclusion of light for 12 hours. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: the dichloromethane (60:40) was further purified. Intermediate 15 was obtained in a yield of 3.1g (90% yield).
Intermediate 15(2.4g, 3.2mmol, 1eq), phenylboronic acid (1.1g, 9.5mmol, 3eq), palladium tetratriphenylphosphine (167mg, 0.13mmol, 0.04eq) and potassium carbonate (1.3g, 9.5mmol, 3eq) were dispersed in 30mL of toluene under nitrogen and reacted at 100 ℃ for 12 hours. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: the dichloromethane (90:10) was further purified. The product was obtained (10-205) in a yield of 1.0g (40% yield).
EXAMPLE 15 synthetic preparation of the first Compounds (10-222)
Under a nitrogen atmosphere, m-bromoiodobenzene (5.0g, 17.6mmol, 1eq) and 2-amino-1-bromonaphthalene (43.2g, 19.4mmol, 1.2eq) were dispersed in 30mL of toluene. Sodium tert-butoxide (5.1g, 53mmol, 3eq), palladium acetate (2 mol%) and 1,1 '-binaphthyl-2, 2' -bis-diphenylphosphine (4 mol%) were then added. After the addition was complete, the temperature was raised to 110 ℃ for 16 hours. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: dichloromethane (95:5) was further purified. Intermediate 17 was obtained in 5.6g yield (85% yield).
Intermediate 17(5.0g, 13.2mmol, 1eq), palladium acetate (2 mol%) and potassium acetate (8.9g, 39.7mmol, 3eq) were dispersed in 30mL of toluene under nitrogen and reacted at 160 ℃ for 14 h. After the reaction was completed, the reaction mixture was cooled to room temperature, and water was added thereto and stirred for 1 hour to form a solid. Pump filtration and subsequent washing with a small amount of ethanol gave intermediate 18 in a yield of 3.5g (88% yield).
Intermediate 18(3.0g, 10.0mmol, 1eq), phenylboronic acid (1.5g, 12.1mmol, 1.2eq), tetrakis (triphenylphosphine) palladium (5 mol%) and potassium carbonate (2.8g, 20mmol, 2eq) were dispersed in 30mL of toluene and 15mL of ethanol under nitrogen and reacted at 120 ℃ for 12 h. Extracted with dichloromethane and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and the crude product was further purified by column chromatography using petroleum ether: dichloromethane (50:50) to give intermediate 19 in 2.3g (78% yield).
Intermediate 19(2.5g, 8.5mmol, 1eq), sodium chloride (7.4g, 127.8mmol, 15eq) and aluminium trichloride (34.0g, 255.6mmol, 30eq) were dissolved in 30mL of toluene under nitrogen atmosphere, washed with water and aqueous sodium bicarbonate solution after hydrolysis, dried over magnesium sulfate and concentrated. The crude product was purified by column chromatography using petroleum ether: further purification of dichloromethane (30:70) gave intermediate 20 in a yield of 0.7g (30% yield).
Intermediate 16(2.1g, 3.2mmol, 1eq), 20(1.5g, 3.8mmol, 1.2eq), cuprous iodide (13mg, 0.06mmol, 0.02eq), phenanthroline (12mg, 0.06mmol, 0.02eq) and potassium carbonate (0.6g, 9.5mmol, 1.5eq) were dispersed in 10mL of azomethylpyrrolidone under a nitrogen atmosphere and reacted at 180 ℃ for 16 hours. After the reaction is finished, adding water and dichloromethane for extraction, collecting an organic phase, spin-drying a solvent, and performing column chromatography on a crude product by using petroleum ether: the dichloromethane (40:60) was further purified. The product (10-222) was obtained in a yield of 1.7g (60% yield).
EXAMPLE 16 synthetic preparation of the first Compound (10-231)
4-Aminodibenzofuran (1.7g, 9.5mmol, 1eq), 3-bromodibenzofuran (2.8g, 11.4mmol, 1.2eq), tris (dibenzylideneacetone) dipalladium (173mg, 0.19mmol, 0.02eq), 1, 1' -bis (diphenylphosphino) ferrocene (107mg, 0.19mmol, 0.02eq) and sodium tert-butoxide (1.3g, 14.2mmol, 1.5eq) were dispersed in 20mL of toluene under a nitrogen atmosphere. The reaction was carried out at 120 ℃ for 16 hours. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: dichloromethane (50:50) was further purified. Intermediate 21 was obtained in a yield of 2.9g (90% yield).
Intermediate 8(2.5g, 3.2mmol, 1eq), intermediate 21(2.9g, 9.5mmol, 3eq), cuprous iodide (25mg, 0.13mmol, 0.04eq), phenanthroline (23mg, 0.13mmol, 0.04eq) and potassium carbonate (1.3g, 9.5mmol, 3eq) were dispersed in 10mL of azomethylpyrrolidone under a nitrogen atmosphere and reacted at 180 ℃ for 16 hours. After the reaction is finished, adding water and dichloromethane for extraction, collecting an organic phase, spin-drying a solvent, and performing column chromatography on a crude product by using petroleum ether: dichloromethane (50:50) was further purified. The product was obtained (10-231) in a yield of 1.2g (30% yield).
EXAMPLE 17 synthetic preparation of the first Compound (10-240)
Compound 10-1(3g, 4.7mmol, 1eq) was dispersed in 30mL of chloroform under a nitrogen atmosphere, followed by dropwise addition of liquid bromine (0.89g, 4.68mmol, 1.2eq) at 0 ℃ and then warming to room temperature for 12 hours. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: the dichloromethane (60:40) was further purified. Intermediate 22 was obtained in a yield of 2.7g (80% yield).
Intermediate 22(2.5g, 3.2mmol, 1eq), (9, 9-dimethyl-9H-fluoren-3-yl) boronic acid (2.3g, 9.5mmol, 3eq), palladium tetratriphenylphosphine (167mg, 0.13mmol, 0.04eq) and potassium carbonate (1.3g, 9.5mmol, 3eq) were dispersed in 30mL toluene under nitrogen atmosphere and reacted at 100 ℃ for 12 hours. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: dichloromethane (80:20) was further purified. The product was obtained (10-240) in a yield of 1.6g (40% yield).
EXAMPLE 18 synthetic preparation of the first Compound (10-248)
2-amino-9, 9 '-diphenylfluorene (3.1g, 9.5mmol, 1eq), iodobenzene (2.3g, 11.4mmol, 1.2eq), tris (dibenzylideneacetone) dipalladium (173mg, 0.19mmol, 0.02eq), 1, 1' -bis (diphenylphosphino) ferrocene (107mg, 0.19mmol, 0.02eq) and sodium tert-butoxide (1.3g, 14.2mmol, 1.5eq) were dispersed in 20mL of toluene under a nitrogen atmosphere. The reaction was carried out at 120 ℃ for 16 hours. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: the dichloromethane (90:100) was further purified. Intermediate 23 was obtained in 3.5g yield (90% yield).
Intermediate 22(2.3g, 3.2mmol, 1eq), 23(1.5g, 3.8mmol, 1.2eq), cuprous iodide (13mg, 0.06mmol, 0.02eq), phenanthroline (12mg, 0.06mmol, 0.02eq) and potassium carbonate (0.6g, 9.5mmol, 1.5eq) were dispersed in 10mL of azomethylpyrrolidone under a nitrogen atmosphere and reacted at 180 ℃ for 16 hours. After the reaction is finished, adding water and dichloromethane for extraction, collecting an organic phase, spin-drying a solvent, and performing column chromatography on a crude product by using petroleum ether: the dichloromethane (20:80) was further purified. The product (10-248) was obtained in a yield of 2.0g (60% yield).
EXAMPLE 19 synthetic preparation of the first Compound (10-251)
2-amino-9, 9 '-diphenylfluorene (3.1g, 9.5mmol, 1eq), 4-iodobiphenyl (3.1g, 11.4mmol, 1.2eq), tris (dibenzylideneacetone) dipalladium (173mg, 0.19mmol, 0.02eq), 1, 1' -bis (diphenylphosphino) ferrocene (107mg, 0.19mmol, 0.02eq) and sodium tert-butoxide (1.3g, 14.2mmol, 1.5eq) were dispersed in 20mL of toluene under a nitrogen atmosphere. The reaction was carried out at 120 ℃ for 16 hours. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: the dichloromethane (90:100) was further purified. Intermediate 23 was obtained in a yield of 4.1g (90% yield).
Intermediate 22(2.3g, 3.2mmol, 1eq), 24(1.8g, 3.8mmol, 1.2eq), cuprous iodide (13mg, 0.06mmol, 0.02eq), phenanthroline (12mg, 0.06mmol, 0.02eq) and potassium carbonate (0.6g, 9.5mmol, 1.5eq) were dispersed in 10mL of azomethylpyrrolidone under a nitrogen atmosphere and reacted at 180 ℃ for 16 hours. After the reaction is finished, adding water and dichloromethane for extraction, collecting an organic phase, spin-drying a solvent, and performing column chromatography on a crude product by using petroleum ether: the dichloromethane (40:60) was further purified. The product was obtained (10-251) in a yield of 1.7g (50% yield).
EXAMPLE 20 synthetic preparation of the first Compound (10-297)
Intermediate 18(2.1g, 7.06mmol, 1eq), sodium hydride (NaH) (0.17g, 7.06mmol, 1eq) and 1, 5-dibromo-2, 4-difluorobenzene (1g, 3.67mmol, 0.52eq) were dispersed in 20mL of N, N-Dimethylformamide (DMF) under a nitrogen atmosphere and reacted at 60 ℃ for 12 hours. After the reaction was completed, a large amount of water was added, extraction was performed with dichloromethane, and the organic layer was collected and dried over anhydrous magnesium sulfate. The crude product was purified by column chromatography using petroleum ether: the dichloromethane (90:10) was further purified. Intermediate 31 was obtained in a yield of 1.7g (60% yield).
Under a nitrogen atmosphere, intermediate 31(1.0g, 1.25mmol,1eq), palladium (II) acetate [ Pd (OAc)2](0.14g, 0.63mmol, 0.5eq), triphenylphosphine (PPh)3) A mixture of (0.2g, 0.75mmol, 0.6eq), benzyltriethylammonium chloride (0.57g, 2.5mmol, 2eq) and potassium carbonate (1.73g, 10mmol, 8eq) was dispersed in 20mL of N, N-Dimethylacetamide (DMAC) and reacted at 140 ℃ for 12 hours. After the reaction was completed, a large amount of water was added, extraction was performed with dichloromethane, and the organic layer was collected and dried over anhydrous magnesium sulfate. The crude product was purified by column chromatography using petroleum ether: dichloromethane (90:10) was used as eluent. Intermediate 32 was obtained in a yield of 0.16g (20% yield).
Intermediate 32(2.1g, 3.2mmol, 1eq), diphenylamine (1.6g, 9.5mmol, 3eq), cuprous iodide (25mg, 0.13mmol, 0.04eq), phenanthroline (23mg, 0.13mmol, 0.04eq) and potassium carbonate (1.3g, 9.5mmol, 3eq) were dispersed in 10mL of azomethylpyrrolidone under a nitrogen atmosphere and reacted at 180 ℃ for 16 hours. After the reaction is finished, adding water and dichloromethane for extraction, collecting an organic phase, spin-drying a solvent, and performing column chromatography on a crude product by using petroleum ether: dichloromethane (50:50) was further purified. The product was obtained (10-297) in a yield of 1.3g (50% yield).
EXAMPLE 21 synthetic preparation of the first Compounds (10-305)
Under nitrogen atmosphere, compound 10-20(2.3g, 4.7mmol, 1eq) was dispersed in 30mL acetonitrile, after which N-bromosuccinimide (0.84g, 4.68mmol, 1eq) was added in one portion and reacted at room temperature for 12 hours with exclusion of light. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: the dichloromethane (60:40) was further purified. Intermediate 33 was obtained in a yield of 2.0g (75% yield).
4-aminobiphenyl (1.6g, 9.5mmol, 1eq), 4-iododibenzothiophene (3.5g, 11.4mmol, 1.2eq), tris (dibenzylideneacetone) dipalladium (173mg, 0.19mmol, 0.02eq), 1, 1' -bis (diphenylphosphino) ferrocene (107mg, 0.19mmol, 0.02eq) and sodium tert-butoxide (1.3g, 14.2mmol, 1.5eq) were dispersed in 20mL of toluene under a nitrogen atmosphere. The reaction was carried out at 120 ℃ for 16 hours. After the reaction is finished, the solvent is dried in a spinning mode, and the crude product is subjected to column chromatography by using petroleum ether: dichloromethane (50:50) was further purified. Intermediate 34 was obtained in a yield of 3.0g (90% yield).
Intermediate 33(1.8g, 3.2mmol, 1eq), 34(1.3g, 3.8mmol, 1.2eq), cuprous iodide (13mg, 0.06mmol, 0.02eq), phenanthroline (12mg, 0.06mmol, 0.02eq) and potassium carbonate (0.6g, 9.5mmol, 1.5eq) were dispersed in 10mL of azomethylpyrrolidone under a nitrogen atmosphere and reacted at 180 ℃ for 16 hours. After the reaction is finished, adding water and dichloromethane for extraction, collecting an organic phase, spin-drying a solvent, and performing column chromatography on a crude product by using petroleum ether: dichloromethane (50:50) was further purified. The product (10-305) was obtained in a yield of 1.3g (50% yield).
EXAMPLE 22 preparation of electroluminescent element
(1) A glass substrate having a thickness of 30mm X0.7 mm and provided with an ITO transparent electrode (anode layer, ITO film thickness is 95nm) was subjected to ultrasonic cleaning in acetone, a cleaning solution, ultrapure water (3 times), and isopropyl alcohol in this order, and the ultrasonic cleaning time in each step was 10 min. And placing the cleaned ITO glass substrate in an oven at 80 ℃ for baking for 3 h. And carrying out vacuum plasma cleaning treatment on the baked ITO glass substrate for 10 min.
(2) The glass substrate after the plasma treatment was mounted on a substrate holder of a vacuum evaporation apparatus, and first, a compound HATCN was evaporated on the surface on which the transparent electrode line was formed so as to cover the transparent electrode, thereby forming a hole injection layer having a thickness of 10 nm.
(3) A compound HT-1 was deposited on the hole injection layer by evaporation to form a first hole transport layer having a thickness of 100 nm. A compound HT-45 was deposited on the first hole transport layer by evaporation to form a second hole transport layer having a thickness of 10 nm.
(4) Second compounds (16-103) (host materials) and first compounds (10-71) (dopant materials) were co-evaporated on the second hole transport layer to form a light emitting layer with a thickness of 25nm, and the mass concentration of the first compounds was 3%.
(5) ET-13 is deposited on the light-emitting layer to form a first electron transport layer with a thickness of 10nm, and Liq and ET-1 are co-deposited on the first electron transport layer, with the mass concentration of Liq being 50%, to form a second electron transport layer with a thickness of 15 nm.
(6) LiF is vapor-deposited on the second electron transport layer to form an electron injection layer having a thickness of 1nm, and metal Al is vapor-deposited on the electron injection layer to form a cathode layer having a thickness of 100 nm.
EXAMPLE 23 preparation of electroluminescent element
The procedure and conditions were the same as in example 22 except that the first compound used (10-71) and the second compound used (16-23).
EXAMPLE 24 preparation of electroluminescent element
The procedure and conditions were the same as in example 22 except that the first compound used (10-90) and the second compound used (16-103).
EXAMPLE 25 preparation of electroluminescent element
The procedure and conditions were the same as in example 22 except that the first compound used (10-109) and the second compound used (16-103).
EXAMPLE 26 preparation of electroluminescent element
The procedure and conditions were the same as in example 22 except that the first compound used (10-124) and the second compound used (16-103).
EXAMPLE 27 preparation of electroluminescent element
The procedure and conditions were the same as in example 22 except that the first compound used (10-179) and the second compound used (16-103).
EXAMPLE 28 preparation of electroluminescent element
The procedure and conditions were the same as in example 22 except that the first compound used (10-245) and the second compound used (16-103).
EXAMPLE 29 preparation of electroluminescent element
The procedure and conditions were the same as in example 22 except that the first compound used (10-245) and the second compound used (16-23).
EXAMPLE 30 preparation of electroluminescent element
The procedure and conditions were the same as in example 22 except that the light-emitting layer used 0.5 wt% of the first compound (10-71), 94.5 wt% of the second compound (16-23), and 5 wt% of the third compound (16-175).
EXAMPLE 31 preparation of electroluminescent element
The procedure and conditions were the same as in example 22 except that the light-emitting layer used 0.5 wt% of the first compound (10-81), 94.5 wt% of the second compound (16-23), and 5 wt% of the third compound (16-175).
EXAMPLE 32 preparation of electroluminescent element
The procedure and conditions were the same as in example 22 except that the light-emitting layer used 0.5 wt% of the first compound (10-179), 94.5 wt% of the second compound (16-23), and 5 wt% of the third compound (16-175).
EXAMPLE 33 preparation of electroluminescent element
The procedure and conditions were the same as in example 22 except that the light-emitting layer used 0.5 wt% of the first compound (10-271), 94.5 wt% of the second compound (16-23), and 5 wt% of the third compound (16-175).
Comparative example 1
The procedure and conditions were the same as in example 22 except that comparative compound 1 was used as the first compound and (16-103) was used as the second compound.
Comparative example 2
The procedure and conditions were the same as in example 22 except that comparative compound 2 was used as the first compound and (16-103) was used as the second compound.
Comparative example 3
The procedure and conditions were the same as in example 22 except that comparative compound 1 was used as the first compound and (16-23) was used as the second compound.
Comparative example 4
The procedure and conditions were the same as in example 22 except that comparative compound 2 was used as the first compound and (16-23) was used as the second compound.
Comparative example 5
The procedure and conditions were the same as in example 22 except that the light-emitting layer used 0.5 wt% of comparative compound 1, 94.5 wt% of the second compound (16-23), and 5 wt% of the third compound (16-175).
Comparative example 6
The procedure and conditions were the same as in example 22 except that the light-emitting layer used 0.5 wt% of comparative compound 2, 94.5 wt% of the second compound (16-23), and 5 wt% of the third compound (16-175).
Of comparative examples 1 to 6, comparative compound 1 and comparative compound 2 have the following structural formulae:
elemental analysis and atomic weight analysis were performed on the first compounds obtained in examples 1 to 21, and table 1 was obtained.
Table 1 elemental analysis and atomic weight analysis of first compounds of examples 1 to 21
| Compound (I) | Elemental analysis (%) | Molecular weight | |
| Example 1 | 10-1 | C，90.53；H，5.08；N，4.40 | 636.28 |
| Example 2 | 10-17 | C，86.29；H，3.46；N，4.78；O，5.47 | 584.18 |
| Example 3 | 10-20 | C，90.44；H，3.99；N，5.57 | 504.20 |
| Example 4 | 10-21 | C，92.26；H，4.57；N，3.18 | 884.32 |
| Example 5 | 10-38 | C，91.37；H，5.12；N，3.55 | 788.29 |
| Example 6 | 10-61 | C，91.73；H，5.54；N，2.73 | 1020.49 |
| Example 7 | 10-71 | C，89.00；H，5.20；N，5.80 | 970.47 |
| Example 8 | 10-90 | C，89.81；H，5.54；N，4.66 | 1203.54 |
| Example 9 | 10-109 | C，90.23；H，4.99；N，4.78 | 1170.44 |
| Example 10 | 10-124 | C，90.82；H，4.82；N，4.35 | 1294.49 |
| Example 11 | 10-162 | C，90.37；H，5.10；N，4.53 | 929.30 |
| Example 12 | 10-179 | C，89.15；H，4.88；N，4.33；O，1.64 | 969.37 |
| Example 13 | 10-191 | C，90.60；H，5.18；N，4.22 | 993.36 |
| Example 14 | 10-205 | C，86.45；H，3.52；N，3.05；O，6.98 | 916.21 |
| Example 15 | 10-222 | C，87.99；H，3.56；N，4.81；O，3.65 | 873.30 |
| Example 16 | 10-231 | C，86.60；H，4.41；N，4.20；O，4.80 | 1330.55 |
| Example 17 | 10-240 | C，91.27；H，5.36；N，3.37 | 828.35 |
| Example 18 | 10-248 | C，90.88；H，5.10；N，4.02 | 1043.40 |
| Example 19 | 10-251 | C，91.12；H，5.13；N，3.75 | 1119.47 |
| Example 20 | 10-297 | C，88.76；H，4.57；N，6.67 | 838.22 |
| Example 21 | 10-305 | C，87.20；H，4.12；N，4.93；S，3.74 | 853.29 |
As is clear from table 1, the organic compounds synthesized as described above were the target compounds.
Photoluminescence spectra were measured for the light-emitting layer materials obtained in examples 27 and 28, respectively, to obtain FIGS. 3 and 4, respectively, which showed narrow emission spectra with half-peak widths of 29nm and 22nm, respectively.
The following tests were carried out on the electroluminescent elements of examples 22 to 33 and comparative examples 1 to 6: measurement was made using a spectroradiometer CS-2000(Konica Minolta) and a digital source meter 2420(Keithley) at a current density of 10mA/cm2CIE1931 chromaticity coordinates (x, y), external quantum efficiency and half-peak width (unit: nm) of electroluminescence spectrum when the prepared organic electroluminescence device was driven, to obtain Table 2.
TABLE 2 electroluminescent element Performance test
| CIE(x，y) | External quantum efficiency of device (%) | Spectrum half-peak width (nm) | |
| Example 22 | 0.14，0.13 | 6.4 | 27 |
| Example 23 | 0.14，0.13 | 7.0 | 28 |
| Example 24 | 0.14，0.14 | 6.7 | 28 |
| Example 25 | 0.14，0.10 | 5.8 | 25 |
| Example 26 | 0.15，0.12 | 6.0 | 30 |
| Example 27 | 0.14，0.13 | 5.5 | 29 |
| Example 28 | 0.14，0.09 | 6.9 | 22 |
| Example 29 | 0.14，0.09 | 7.1 | 21 |
| Example 30 | 0.14，0.12 | 9.6 | 26 |
| Example 31 | 0.15，0.13 | 9.2 | 30 |
| Example 32 | 0.14，0.13 | 8.8 | 28 |
| Example 33 | 0.14，0.11 | 9.5 | 23 |
| Comparative example 1 | 0.16，0.26 | 5.2 | 57 |
| Comparative example 2 | 0.15，0.22 | 5.0 | 55 |
| Comparative example 3 | 0.16，0.27 | 5.3 | 58 |
| Comparative example 4 | 0.16，0.23 | 5.1 | 54 |
| Comparative example 5 | 0.16，0.24 | 8.3 | 54 |
| Comparative example 6 | 0.15，0.20 | 7.9 | 50 |
As can be seen from table 2, the half-widths of the spectra of the first compounds of the examples of the present invention are significantly reduced as compared with the comparative compounds 1 and 2, and the half-widths of the spectra of the compounds of the present invention are both 30nm or less. The reason is that after ring formation modification is introduced into an indolocarbazole molecular skeleton, molecular vibration and energy state conformation relaxation which cause spectral broadening can be effectively inhibited, so that the vibration spectral intensity in an emission spectrum is reduced, and the narrow emission spectral characteristic is shown. While the emission spectra of comparative compounds 1 and 2 present a more pronounced vibrational spectral structure, which generally results in a broader emission spectral characteristic. On the other hand, the external quantum efficiency of the electroluminescent element of the embodiment of the invention is higher than that of the electroluminescent element prepared by the comparative compound 1 and the comparative compound 2, because the introduced ring-forming modification unit inhibits the non-radiative vibration of molecules, enhances the transition dipole strength of the compound, and improves the fluorescence quantum yield of the luminescent compound, thereby having a synergistic improvement effect on the external quantum efficiency of the device.
The above is only a preferred embodiment of the present invention, and it is not intended to limit the scope of the invention, and various modifications and changes will occur to those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention shall be included in the scope of the present invention.
Claims (19)
1. A light-emitting layer material is characterized by comprising a first compound, wherein the structural general formula of the first compound is shown as a structural formula (1):
wherein the ring-forming atoms bonded to the ring a and the ring b are at least one selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, silicon atoms, boron atoms, sulfur atoms, selenium atoms and selenium atoms, R0、R1、R2、R3、R6、R7、R8、R9、R10、R13、R14、R15Each independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, amino group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atomsA fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring-forming carbon atoms, -N (R)101)(R102) R is any one of a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms0、R1、R2、R3、R6、R7、R8、R9、R10、R13、R14、R15The substituents of (a) are not bonded to each other or are bonded to each other to form a ring structure;
R101and R102Each independently is any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms.
2. The light-emitting layer material according to claim 1, wherein each of the rings a and b is independently selected from any one of structural formulae (2) to (9):
wherein each pair of 1 and 2,3 and 4, 5 and 6,7 and 8, 9 and 10, 11 and 12, 13 and 14, and 15 and 16 represents 2 ring-forming carbon atoms to which ring a and ring b are bonded, respectively;
R21～R33each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, an amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atomsSubstituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 ring-forming carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 ring-forming carbon atoms, -N (R)101)(R102) R is any one of a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms21～R33Wherein adjacent groups are not bonded to each other or bonded to each other to form a ring structure;
x and Y are each independently selected from C (R)41)(R42)、NR43、O、S、Se、Si，R101、R102、R41、R42、R43Each independently is any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms.
3. The light-emitting layer material according to claim 1 or 2, wherein each of the rings a and b is independently selected from any one of structural formulae (2), (10), (11):
wherein each pair of 1 and 2,3 and 4, and 7 and 8 represents 2 ring-forming carbon atoms to which ring a and ring b are bonded, respectively;
x and Y are each independently selected from C (R)41)(R42)、NR43、O、S、Se、Si，R21、R22、R23、R24、R51、R52、R53、R54、R55、R56、R57、R58Each independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, and substituted or unsubstituted carbonAn alkynyl group having a number of 1 to 20, a cycloalkyl group having a substituted or unsubstituted ring-forming carbon number of 3 to 20, an amino group, an alkoxy group having a substituted or unsubstituted carbon number of 1 to 20, a fluoroalkyl group having a substituted or unsubstituted carbon number of 1 to 20, a fluoroalkoxy group having a substituted or unsubstituted carbon number of 1 to 20, an aryloxy group having a substituted or unsubstituted ring-forming carbon number of 6 to 50, an alkylthio group having a substituted or unsubstituted carbon number of 1 to 20, an arylthio group having a substituted or unsubstituted ring-forming carbon number of 6 to 50, and-N (R)101)(R102) R is any one of a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms21、R22、R23、R24、R51、R52、R53、R54、R55、R56、R57、R58Wherein adjacent groups are not bonded to each other or bonded to each other to form a ring structure;
R41、R42、R43、R101、R102each independently is any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms.
4. The light-emitting layer material according to claim 1 or 2, wherein each of the rings a and b is independently selected from any one of structural formulae (21) to (24):
wherein 1 and 2 represent 2 ring-forming carbon atoms to which ring a and ring b are bonded, respectively;
R61、R62、R63、R64、R65、R66、R67、R68、R69、R71、R72、R73、R74、R75、R76、R78each independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, amino group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, -N (R)101)(R102) R is any one of a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms61、R62、R63、R64、R65、R66、R67、R68、R69、R71、R72、R73、R74、R75、R76、R78Wherein adjacent groups are not bonded to each other or bonded to each other to form a ring structure;
R101and R102Each independently is any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms.
5. The luminescent layer material according to any one of claims 1 to 4, wherein R is R0、R1、R2、R3、R6、R7、R8、R9、R10、R13、R14、R15Each independently selected from any one of structural formulas (30) to (37):
wherein X and Y are each independently selected from C (R)41)(R42)、NR43、O、S、Se、Si，RC、Ar1、Ar2Each independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, amino group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, -N (R)101)(R102) Any one of substituted or unsubstituted aryl with 6-50 ring-forming carbon atoms and substituted or unsubstituted heteroaryl with 5-50 ring-forming carbon atoms, wherein P1 is an integer of 0-5, P2 is an integer of 0-4, and P3 is an integer of 0-3;
R41、R42、NR43、R101and R102Each independently is any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms;
l is any one of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms.
6. The luminescent layer material of claim 5, wherein R is0、R1、R2、R3、R6、R7、R8、R9、R10、R13、R14、R15Each independently selected from any one of structural formulas (50) to (54)The method comprises the following steps:
wherein X and Y are each independently selected from C (R)41)(R42)、NR43O, S, Se, Si, in the formulae (53) and (54), RnAnd Rn+1Are bonded to each other to form a ring structure selected from the group consisting of the ring structures of formula (55) or (56), or RnAnd Rn+1Not bonded to each other and not forming a ring, n represents an integer selected from 80 to 82, 84 to 86, each of pairs of 1 and 2 and 3 and 4 represents RnAnd Rn+12 ring-forming carbon atoms of the ring structure to which it is bonded;
RC、R90～R97each independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, amino group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, -N (R)101)(R102) Any one of substituted or unsubstituted aryl with 6-50 ring-forming carbon atoms and substituted or unsubstituted heteroaryl with 5-50 ring-forming carbon atoms, wherein P1 is an integer of 0-5, P2 is an integer of 0-4, and P4 is an integer of 0-3;
R41、R42、NR43、R101and R102Each independently is any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms;
l is any one of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms.
7. The light-emitting layer material according to claim 1, wherein the first compound is selected from any one of structural formulae (1-1) to (1-3):
wherein X is selected from C (R)41)(R42)、NR43、O、S、Se、Si，R0～R3、R6、R8～R10、R13～R15、R100～R107、R110～R117Each independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, amino group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, -N (R)111)(R112) R is any one of a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms0～R3、R6、R8～R10、R13～R15、R100～R107、R110～R117Wherein adjacent groups are not bonded to each other or bonded to each other to form a ring structure;
R41、R42、R43、R111、R112each independently is any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms.
8. The light-emitting layer material according to claim 7, wherein the first compound represented by the structural formula (1-2) is selected from any one of structural formulae (8-1) to (8-3):
wherein X is selected from C (R)41)(R42)、NR43、O、S、Se、Si，R0、R3、R6、R7、R13～R15、R100～R107、R170～R177Each independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, amino group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, -N (R)111)(R112) R is any one of a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms13～R15、R100～R107、R170～R177Wherein adjacent groups are not bonded to each other or bonded to each other to form a ring structure;
R41、R42、R43、R111、R112each independently is any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms.
9. The luminescent layer material according to claim 7 or 8, wherein R is R0～R3、R6、R8～R10、R13～R15Each independently selected from any one of structural formulas (50) to (54):
wherein X and Y are each independently selected from C (R)41)(R42)、NR43O, S, Se, Si, in the formulae (53) and (54), RnAnd Rn+1Are bonded to each other to form a ring structure selected from the group consisting of the ring structures of formula (55) or (56), or RnAnd Rn+1Not bonded to each other and not forming a ring, n represents an integer selected from 80 to 82, 84 to 86, each of pairs of 1 and 2 and 3 and 4 represents RnAnd Rn+12 ring-forming carbon atoms of the ring structure to which it is bonded;
RC、R90～R97each independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, amino group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, -N (R)101)(R102) Substituted or unsubstituted C6-50 in ring formationAny one of an aryl group and a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, wherein P1 is an integer of 0 to 5, P2 is an integer of 0 to 4, and P4 is an integer of 0 to 3;
R41、R42、NR43、R101and R102Each independently is any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms;
l is any one of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms.
10. The light-emitting layer material according to claim 1, wherein the first compound is selected from any one of structural formulae (10-1) to (10-344):
11. the light-emitting layer material according to claim 1, wherein the light-emitting layer material further comprises a second compound and/or a third compound, and wherein each of the second compound and the third compound comprises a compound having a polycyclic aromatic skeleton.
12. The light-emitting layer material according to claim 11, wherein the second compound comprises anthracene and a derivative thereof,
And derivatives thereof, imidazole and derivatives thereof, pyrene and derivatives thereof, fluorene and derivatives thereof; and/or the presence of a gas in the gas,
the third compound comprises anthracene and derivatives thereof,
And derivatives thereof, imidazole and derivatives thereof, pyrene and derivatives thereof, fluorene and derivatives thereof.
13. The light-emitting layer material according to claim 11, wherein the third compound comprises at least one of triazine and a derivative thereof, pyrimidine and a derivative thereof, pyridine and a derivative thereof, boron and a derivative thereof, a thiamphen group and a derivative thereof, a compound having a skeleton of benzonitrile and a derivative thereof, quinoxaline and a derivative thereof, phosphorus-oxygen-containing and a derivative thereof, and benzophenone and a derivative thereof.
14. The light-emitting layer material according to claim 12, wherein the anthracene and the derivative thereof are selected from the structural formula (60):
wherein R is180～R189Independently from each other, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms in a ring, an amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms in a ring, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 carbon atoms in a ring, and-N (R is an aromatic hydrocarbon group101)(R102) A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms, -Ar or-L2-Ar, and R180～R189At least one of them is-Ar or-L2-Ar；
R101And R102Each independently is a hydrogen atom, a deuterium atom, a substituted orAn unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms, L2The aromatic ring is selected from any one of substituted or unsubstituted arylene with 6-30 ring carbon atoms and substituted or unsubstituted heteroarylene with 5-30 ring carbon atoms, and Ar is selected from any one of substituted or unsubstituted monocyclic group with 5-50 ring carbon atoms, substituted or unsubstituted condensed ring group with 8-50 ring carbon atoms and group formed by the combination of the monocyclic group and the condensed ring group.
15. The light-emitting layer material according to claim 12, wherein the pyrene and the derivative thereof are selected from the structural formula (61):
wherein R is190～R199Independently from each other, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms in a ring, an amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms in a ring, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 carbon atoms in a ring, and-N (R is an aromatic hydrocarbon group101)(R102) A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms, -Ar or-L3-Ar, and R180～R189At least one of them is-Ar or-L3-Ar；
R101And R102Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cyclic carbon number of 3 to 20A cycloalkyl group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming carbon atoms, L3The aromatic ring is selected from a single-bond substituted or unsubstituted arylene group with 6-30 ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group with 5-30 ring-forming carbon atoms, and Ar is selected from any one of a substituted or unsubstituted monocyclic group with 5-50 ring-forming carbon atoms, a substituted or unsubstituted fused ring group with 8-50 ring-forming carbon atoms and a group consisting of a combination of the monocyclic group and the fused ring group.
16. The light-emitting layer material according to any one of claims 11 to 15, wherein the second compound and the third compound are each independently selected from any one of structural formulae (16-1) to (16-190):
17. the light-emitting layer material according to any one of claims 11 to 15, wherein the light-emitting layer material comprises a first compound in a mass fraction of 0.1% to 20% and a second compound in a mass fraction of 80% to 99.9%; and/or the light-emitting layer material comprises 0.1-10% of a first compound by mass, 20-94.9% of a second compound by mass and 5-79.9% of a third compound by mass.
18. An organic electroluminescent device, comprising a substrate, an anode layer, an organic light-emitting functional layer and a cathode layer which are sequentially stacked from bottom to top, wherein the organic light-emitting functional layer comprises a hole injection layer, a hole transport layer, an electron transport layer and an electron injection layer which are sequentially stacked from bottom to top, and a light-emitting layer, the light-emitting layer is located between the hole transport layer and the electron transport layer, the hole transport layer is composed of a first hole transport layer and/or a second hole transport layer, the electron transport layer is composed of a first electron transport layer and/or a second electron transport layer, and the material of the light-emitting layer comprises the light-emitting layer material according to any one of claims 1 to 17.
19. An electronic device characterized in that it comprises the organic electroluminescent device according to claim 18.
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| CN (1) | CN114195794A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115418216A (en) * | 2022-08-31 | 2022-12-02 | 季华恒烨(佛山)电子材料有限公司 | Light-emitting composition and organic electroluminescent device |
| CN118084927A (en) * | 2024-04-19 | 2024-05-28 | 季华恒烨(佛山)电子材料有限公司 | Indolocarbazole compound and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112778309A (en) * | 2019-11-06 | 2021-05-11 | 广州华睿光电材料有限公司 | N-containing condensed ring compound and application thereof in organic electronic device |
| JP2021134172A (en) * | 2020-02-27 | 2021-09-13 | 出光興産株式会社 | Compounds, organic electroluminescence devices and electronic devices using them |
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2021
- 2021-11-16 CN CN202111359241.1A patent/CN114195794A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112778309A (en) * | 2019-11-06 | 2021-05-11 | 广州华睿光电材料有限公司 | N-containing condensed ring compound and application thereof in organic electronic device |
| JP2021134172A (en) * | 2020-02-27 | 2021-09-13 | 出光興産株式会社 | Compounds, organic electroluminescence devices and electronic devices using them |
Non-Patent Citations (1)
| Title |
|---|
| VILAS VENUNATH PATIL, ET AL.: ""Strategic Synchronization of 7,7-Dimethyl-5,7-dihydroindeno[2,1‑b]carbazole for Narrow-Band, Pure Violet Organic Light-Emitting Diodes with an Efficiency of > 5% and a CIE y Coordinate of < 0.03"", 《ACS APPL. MATER. INTERFACES》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115418216A (en) * | 2022-08-31 | 2022-12-02 | 季华恒烨(佛山)电子材料有限公司 | Light-emitting composition and organic electroluminescent device |
| CN118084927A (en) * | 2024-04-19 | 2024-05-28 | 季华恒烨(佛山)电子材料有限公司 | Indolocarbazole compound and application thereof |
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Application publication date: 20220318 |