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Definitions

• the present application relates to an organic electroluminescence device and a display device, which belong to the technical field of organic electroluminescence.
• Organic Light Emitting Diode (Organic Light Emitting Diode, referred to as OLED) is a device that is driven by current to achieve the purpose of emitting light. Its main characteristics come from the organic light-emitting layer. When an appropriate voltage is applied, electrons and holes Excitons are combined in the organic light-emitting layer to emit light of different wavelengths according to the characteristics of the organic light-emitting layer.
• the light-emitting layer is composed of host materials and dyes, and the dyes are mostly selected from traditional fluorescent materials and traditional phosphorescent materials.
• the traditional phosphorescent material has high efficiency, it is expensive and has poor stability, while the traditional fluorescent material is cheap but extremely low in efficiency.
• Existing display devices still have problems such as low efficiency and high driving voltage.
• the present application provides an organic electroluminescent device and a display device, which have high luminous efficiency and driving voltage stability.
• the application provides an organic electroluminescent device, which comprises a light-emitting layer, and the light-emitting layer comprises a triplet-triplet annihilation host and a fluorescent dye, wherein the fluorescent dye has the following formula (1) Or the structure shown in formula (2):
• X 1 and X 2 are independently represented as O, S or N(R 1 );
• A represents one of substituted or unsubstituted C 6 -C 60 carbocyclic groups, substituted or unsubstituted C 3 -C 60 heterocyclic groups, and A is substituted
• Substitution in carbocyclyl or substituted heterocyclic group refers to being selected from deuterium, tritium, cyano, halogen, C 1 ⁇ C 10 alkyl, C 3 ⁇ C 10 cycloalkyl, silicon, C 6 ⁇ C 30 arylamino group, C 6 ⁇ C 30 aryl group, C 2 ⁇ C 30 heteroaryl group, or a combination of at least two of them, the substituent is independently connected to the aromatic ring or heteroaryl
• the rings are connected to form a ring or not to form a ring;
• Z 1 -Z 10 are independently represented as N or CR, each appearance of R is the same or different, and two adjacent R can be bonded to each other to form a ring;
• R 1 is connected to the adjacent R by a single bond
• R 2 is connected to the adjacent R by a single bond
• R 1 represents substituted or unsubstituted C 1 -C 10 alkyl, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 6 -C 30 aryl, substituted or unsubstituted C One of 2 ⁇ C 30 heteroaryl groups;
• R 2 represents one of substituted or unsubstituted C 6 -C 30 aryl, substituted or unsubstituted C 2 -C 30 heteroaryl;
• R represents hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C 1 -C 10 alkyl, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 1 -C 10 alkoxy, substituted or unsubstituted C 6 -C 30 aryloxy, substituted or unsubstituted C 6 -C 30 arylamino, substituted or unsubstituted C 6 -C 30 aryl, substituted or unsubstituted One of the C 2 -C 30 heteroaryl groups;
• R 1 , R 2 , R substituted or unsubstituted in the substituent refers to being selected from deuterium, tritium, cyano, halogen, C 1 ⁇ C 10 alkyl, C 3 ⁇ C 10 cycloalkyl, silicon , C 6 ⁇ C 30 arylamino group, C 6 ⁇ C 30 aryl group, C 2 ⁇ C 30 heteroaryl group or a combination of at least two, the substituent is independently connected to the aromatic ring Or the heteroaryl rings are linked to form a ring or not linked to form a ring.
• the present application also provides a display device, comprising any one of the organic electroluminescent devices described above.
• the light-emitting layer includes a triplet-triplet-annihilation material and a fluorescent dye with a structure represented by formula (1) or formula (2).
• the triplet-triplet-annihilation material with triplet annihilation effect and lower triplet energy level combined with fluorescent dyes with anti-intersystem jumping can realize the efficient use of excitons in the system and reduce the triplet excitation in the system.
• the concentration of electrons can improve the luminous efficiency and driving voltage of the device, and suppress the efficiency roll-off.
• the fluorescent dye of the present application can effectively inhibit the interaction between molecules of planar multiple resonance compounds, inhibit the Dexter energy transfer between host and guest materials in the light-emitting layer and the influence of intermolecular interactions, and further realize the improvement of device luminous efficiency and driving voltage. improve.
• the application provides an organic electroluminescent device, which comprises a light-emitting layer, and the light-emitting layer comprises a triplet-triplet annihilation host and a fluorescent dye, wherein the fluorescent dye has the following formula (1) Or the structure shown in formula (2):
• X 1 and X 2 are independently represented as O, S or N(R 1 );
• A represents one of substituted or unsubstituted C 6 -C 60 carbocyclic groups, substituted or unsubstituted C 3 -C 60 heterocyclic groups, and A is substituted
• Substitution in carbocyclyl or substituted heterocyclic group refers to being selected from deuterium, tritium, cyano, halogen, C 1 ⁇ C 10 alkyl, C 3 ⁇ C 10 cycloalkyl, silicon, C 6 ⁇ C 30 arylamino group, C 6 ⁇ C 30 aryl group, C 2 ⁇ C 30 heteroaryl group or a combination of at least two of them are substituted, and the substituent is independently connected to the aromatic ring (that is, the aforementioned C 6 ⁇ C 60 carbocyclyl) or heteroaromatic ring (ie, the aforementioned C 3 ⁇ C 60 heterocyclic group) is connected to form a ring or not connected to form a ring;
• Z 1 -Z 10 are independently represented as N or CR, each appearance of R is the same or different, and two adjacent R can be bonded to each other to form a ring;
• R 1 is connected to the adjacent R by a single bond
• R 2 is connected to the adjacent R by a single bond
• R 1 represents substituted or unsubstituted C 1 -C 10 alkyl, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 6 -C 30 aryl, substituted or unsubstituted C One of 2 ⁇ C 30 heteroaryl groups;
• R 2 represents one of substituted or unsubstituted C 6 -C 30 aryl, substituted or unsubstituted C 2 -C 30 heteroaryl;
• R represents hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C 1 -C 10 alkyl, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 1 -C 10 alkoxy, substituted or unsubstituted C 6 -C 30 aryloxy, substituted or unsubstituted C 6 -C 30 arylamino, substituted or unsubstituted C 6 -C 30 aryl, One of substituted or unsubstituted C 2 -C 30 heteroaryl groups;
• R 1 , R 2 , R substituted or unsubstituted in the substituent refers to being selected from deuterium, tritium, cyano, halogen, C 1 ⁇ C 10 alkyl, C 3 ⁇ C 10 cycloalkyl, silicon , C 6 ⁇ C 30 arylamino group, C 6 ⁇ C 30 aryl group, C 2 ⁇ C 30 heteroaryl group or a combination of at least two, the substituent is independently connected to the aromatic ring Or the heteroaryl rings are linked to form a ring or not linked to form a ring.
• the expression of Ca ⁇ Cb means that the number of carbon atoms of the group is a ⁇ b, unless otherwise specified, generally speaking, the number of carbon atoms does not include the number of carbon atoms of the substituent.
• the expression of chemical elements usually includes the concept of isotopes with the same chemical properties, such as the expression "hydrogen”, also includes the concepts of "deuterium” and “tritium” with the same chemical properties, carbon ( C) includes 12 C, 13 C, etc., which will not be repeated here.
• the expression of the ring structure crossed by "—" indicates that the linking site is at any position on the ring structure that can form a bond.
• heteroaryl group in the present application refers to an aromatic ring group containing heteroatoms.
• the so-called heteroatoms usually refer to those selected from N, O, S, P, Si and Se, preferably selected from N, O, S .
• C6-C60 aryl group and C3-C60 heteroaryl group in the present application are aromatic groups satisfying the ⁇ -conjugated system, including single ring and condensed ring.
• the so-called single ring means that the molecule contains at least one phenyl group.
• the phenyl groups are independent of each other and connected by a single bond, such as phenyl, biphenyl, triple Phenyl, etc.
• fused ring means that the molecule contains at least two benzene rings, but the benzene rings are not independent of each other, but are fused to each other by sharing ring edges, such as naphthyl, anthracenyl, phenanthrenyl, etc.
• Monocyclic heteroaryl means that the molecule contains at least one heteroaryl group.
• heteroaryl group and other groups such as aryl, heteroaryl, alkyl, etc.
• the groups are independent of each other and connected by a single bond, for example, pyridine, furan, thiophene, etc.
• fused ring heteroaryl refers to the fusion of at least one phenyl and at least one heteroaryl, or, at least Two kinds of heteroaryl groups are fused, such as quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, etc. for example.
• the substituted or unsubstituted C6 ⁇ C60 aryl group is preferably a C6 ⁇ C30 aryl group, and the carbon number of the aryl group includes but not limited to C6, C8, C10, C12, C14, C16, C18, C20, C22 , C24, C26, C28, etc., preferably phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, triphenanthrenyl, pyrenyl, sulfenyl, perylene, fluoranthenyl, and Tetraphenyl, pentaphenyl, benzopyrenyl, biphenyl, biphenyl, terphenyl, triphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, bis Aryl in the group consisting of hydropyrenyl, tetrahydropyr
• biphenyl is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, P-terphenyl-2-yl, inter-terphenyl-4-yl, inter-terphenyl-3-yl and inter-terphenyl-2-yl; said naphthyl includes 1-naphthyl or 2-naphthyl; Anthracenyl is selected from 1-Anthracenyl, 2-Anthracenyl and 9-Anthracenyl; The fluorenyl is selected from 1-Fluorenyl, 2-Fluorenyl, 3-Fluorenyl, 4-Fluorenyl and 9-fluorenyl; said pyrenyl is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; naphthacene is selected
• aromatic ring in the present application, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and derivatives thereof, fluoranthene, triphenyl Phenyl, pyrenyl, perylene, A group in the group consisting of base and naphthacene.
• the biphenyl is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl;
• the terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl , p-terphenyl-2-yl, inter-terphenyl-4-yl, inter-terphenyl-3-yl and inter-terphenyl-2-yl;
• the naphthyl includes 1-naphthyl or 2-naphthyl;
• the anthracenyl is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl;
• the fluorenyl is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3- In the group consisting of fluorenyl, 4-fluorenyl and 9-fluorenyl;
• the fluorenyl derivatives are selected from the group consisting of 9,
• the substituted or unsubstituted C3 ⁇ C60 heteroaryl is preferably a C3 ⁇ C30 heteroaryl.
• the carbon number of heteroaryl includes but not limited to C4, C5, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc. can be nitrogen-containing heteroaryl, oxygen-containing heteroaryl, sulfur-containing heteroaryl, etc.
• heterocycles in the present application include furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, diphenyl Thienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivatives are preferably 9-phenylcarbazole, 9-naphthylcarbazolebenzocarbazole, dibenzocarbazole or indolo Carbazole.
• the C3-C60 heteroaryl group in the present application may also be a group formed by connecting or/and condensing the above groups with a single bond.
• alkyl group including the concepts of straight-chain alkyl group and branched-chain alkyl group as well as cycloalkyl group.
• the number of carbons in the alkyl group includes but is not limited to C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C22, C24, C26, C28, etc.
• the C1-C30 alkyl group is more preferably a C1-C20 alkyl group, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, adamantyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl group, 2-ethylhexyl group, trifluoromethyl group, pentafluoroethyl group, 2,2,2-trifluoroethyl group, etc., more preferably C1-C10 alkyl group.
• cycloalkyl includes monocycloalkyl and polycycloalkyl, and the number of carbons includes but not limited to C4, C5, C6, C7, C8, C9, etc., for example: cyclopropyl, cyclobutyl base, cyclopentyl, cyclohexyl, cycloheptyl, etc.
• examples of C1-C20 alkoxy groups include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy , tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, etc., preferably Methoxy, ethoxy, n-propoxy, isopropoxy, t-butoxy, sec-butoxy, isobutoxy, isopentyloxy, more preferably methoxy.
• examples of C1-C20 silyl groups may be silyl groups substituted by groups listed in the above-mentioned C1-C20 alkyl groups, specifically, methylsilyl, dimethylsilyl Silyl group, trimethylsilyl group, ethylsilyl group, diethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, tert-butyldiphenylsilyl group, etc. group.
• the C6-C60 aryloxy group there can be mentioned groups formed by linking each of the above-mentioned substituted or unsubstituted C6-C60 aryl groups with oxygen.
• groups formed by linking each of the above-mentioned substituted or unsubstituted C6-C60 aryl groups with oxygen for specific examples, please refer to the above-mentioned examples. I won't go into details here.
• halogen examples include fluorine, chlorine, bromine, iodine and the like.
• C6 ⁇ C60 arylamino and C3 ⁇ C60 heteroarylamino it means that one H or two H in amino- NH2 is replaced by the above-mentioned C6 ⁇ C60 aryl or C3 ⁇ C60 heteroaryl The resulting group is substituted by the group.
• the light-emitting layer of the organic electroluminescent device of the present application includes a host material and a fluorescent dye, wherein the host material is a triplet-triplet annihilation material (Tripletthora-triplet annihilation, referred to as: TTA), and the fluorescent dye is formula (1) or formula ( 2) A class of planar multiple resonance compounds with anti-intersystem crossing properties. Specifically, the first excited singlet energy level of the host material is greater than that of the fluorescent dye, and the first excited triplet energy level of the host material is smaller than that of the fluorescent dye.
• TTA triplet-triplet annihilation
• the host material and the fluorescent dye have this energy level relationship, after the organic electroluminescent device is electrically excited, the first excited singlet state excitons of the host material will generate to the first excited singlet state of the lower energy level fluorescent dye. transition, and although the fluorescent dye has the first excited triplet state with a higher energy level, due to its anti-intersystem crossing property, the fluorescent dye will undergo an upconversion process, so its own first excited triplet state excitons, the second excited triplet state The first excited singlet excitons and the first excited singlet excitons from the host material fluoresce by transitioning to the ground state.
• the organic electroluminescent device of the present application can not only effectively utilize triplet excitons, but also have a low concentration of triplet excitons in the system. Therefore, the organic electroluminescent device of the present application has excellent luminous efficiency, and Efficiency roll-off and low drive voltage.
• a carbocyclic group or heterocyclic group represented by A with a large steric hindrance group covering has been introduced into the molecular structures of formula (1) and formula (2), and the large steric hindrance group will not only prevent The luminous color and half-peak width of the mother nucleus have a significant impact, and it can also effectively inhibit the interaction between the molecules of the planar multiple resonance compound, thereby effectively inhibiting the reduction of the luminous efficiency of the compound and the broadening of the spectrum at high concentrations.
• the molecular structures of formulas (1) and (2) can effectively suppress the influence of the host-guest materials in the light-emitting layer, including Dexter energy transfer and intermolecular interactions, which can greatly improve the luminous efficiency of the device and drive
• the voltage is reduced, and the width of the efficiency process window is optimized, which enhances the luminous efficiency and the stability of the driving voltage.
• the chemical synthesis of the fluorescent dyes represented by the formulas (1) and (2) is more feasible, and it is easy to modify a variety of different functions, and further structural adjustments can be made according to different application requirements.
• the fluorescent dye has the following (1-1), (1-2), (1-3), (1-4), (1-5), (1-6), (2 The structure shown in any of -1), (2-2) or (2-3):
• Z 1 -Z 10 are independently represented as CR, and the definitions of A, R, R 1 and R 2 are the same as those in formula (1) or formula (2); preferably, R 1 is the same as Adjacent Rs are connected by single bonds, and R2 is connected with adjacent Rs by single bonds.
• A is represented as a substitution such as the following (3-1), (3-2), (3-3), (3-4), (3-5), (3 Any structural group shown in -6), (3-7), (3-8) or (3-9):
• the asterisk in the above structure indicates the site that can be connected, and the connection indicates that it is connected to the mother core and/or is connected with a substituent group; the expression of the ring structure crossed by "—" indicates that the connection site is on the ring structure Any position capable of forming a bond; the dotted line in the above structural formula indicates connection or non-connection;
• A is a substitution in a substituted structural group, which means that it is selected from deuterium, tritium, cyano, halogen, C 1 ⁇ C 10 alkane Substituted by one or a combination of at least two of C 3 -C 10 cycloalkyl, C 6 -C 30 arylamino, C 6 -C 30 aryl, C 2 -C 30 heteroaryl, the The substituents are independently ring-linked or not linked to the aryl or heteroaryl ring to which they are attached.
• R 3 and R 4 independently represent hydrogen, deuterium, tritium, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 3 -C 30 cycloalkyl, silicon, substituted or Unsubstituted C 1 -C 30 alkoxy, substituted or unsubstituted C 6 -C 60 aryloxy, substituted or unsubstituted C 6 -C 60 arylamino, substituted or unsubstituted C 6 -C 60 Any one of aryl, substituted or unsubstituted C 2 -C 60 heteroaryl; Z is independently represented as N or CR 5 , each appearance of R 5 is the same or different, and two adjacent R 5 can be mutually Bonded to form a ring; R 5 represents hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C 1 -C 10 alkyl, substituted or unsubstituted
• R 3 and R 4 are independently represented as substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 6 - Any one of C 60 aryl, substituted or unsubstituted C 2 -C 60 heteroaryl; preferably, at least one of the above-mentioned R 3 and R 4 is selected from one of the following bulky hindrance groups : terphenyl, triphenyl, quaternyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis or trans indenofluorenyl, trimer Indenyl, isotriindenyl, spiroindenyl, spiroisotriindenyl, furyl, benzofuryl, isobenz
• R represents hydrogen, deuterium, tritium, fluorine atom, cyano group, methyl group, deuterated methyl group, tritiated methyl group, ethyl group, deuterated ethyl group, tritiated ethyl group, Isopropyl, deuterated isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclopentyl, cyclohexyl, cyclo Amyl, adamantyl, phenyl, deuterated phenyl, tritiated phenyl, bisphenyl, deuterated bisphenyl, tritiated bisphenyl, deuterated terphenyl, tritiated terphenyl , terphenyl, naphthyl,
• R is represented by methyl, deuterated methyl, deuterated methyl, ethyl, deuterated ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, deuterated isopropyl, tert-butyl, Deuterated tert-butyl, tritiated tert-butyl, deuterated cyclopentyl, tritiated cyclopentyl, cyclopentyl, adamantyl, phenyl, deuterated phenyl, tritiated phenyl, biphenyl, Deuterated biphenyl, tritiated biphenyl, deuterated terphenyl, tritiated terphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyridyl, quinolinyl, furyl, thiophene Base, dibenzofuryl, dibenzo
• R2 represents phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, deuterated terphenyl, tritiated terphenyl, terphenyl Base, naphthyl, anthracenyl, phenanthrenyl, pyridyl, quinolinyl, dibenzofuryl, dibenzothienyl, N-phenylcarbazolyl, methyl-substituted phenyl, micyl, ethyl Substituted phenyl, isopropyl substituted phenyl, tert-butyl substituted phenyl, methyl substituted biphenyl, ethyl substituted biphenyl, isopropyl substituted biphenyl, tert Butyl substituted biphenyl, deuterated methyl substituted phenyl, deuterated ethy
• both Z 9 and Z 10 are CR, and the R is hydrogen, Z 1 -Z 8 are all CR, and the definition of R is the same as The definitions in formula (1) or formula (2) are the same.
• Z 2 and Z 7 are both CR, and R is tert-butyl, Z 1 , Z 3 -Z 6 , Z 8 -Z 10 are all CR, and the R is hydrogen.
• fluorescent dyes of the present application are selected from the following specific structural compounds:
• the present application does not specifically limit the TTA host material in the light-emitting layer.
• the performance of the organic electroluminescent device can be improved more significantly.
• the mass proportion of the fluorescent dye in the light-emitting layer is generally controlled to be 0.1% to 50%.
• Reasonable control of the doping amount of the dye in the light-emitting layer is conducive to further improving the luminous efficiency of the device.
• different host materials and dyes in the light-emitting layer of the organic electroluminescent device of the present application will affect the performance of the device. Therefore, generally speaking, for different host materials and dyes, when the mass proportion of the dye in the light-emitting layer is controlled at 0.5% to 20%, the excellent luminous efficiency of the device can be basically guaranteed.
• the thickness of the light-emitting layer of the organic electroluminescent device of the present application is not particularly limited, and may be consistent with the thickness of the light-emitting layer of existing devices in the field, for example, 10-60 nm.
• the organic electroluminescent device of the present application also includes an anode on one side of the light emitting layer and a cathode on the other side of the light emitting layer, that is, the light emitting layer is located between the cathode and the anode.
• the anode and the cathode can adopt materials commonly used in this field.
• the anode can use oxide transparent conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO 2 ), zinc oxide (ZnO) and any combination thereof;
• the cathode can use magnesium (Mg ), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and other metals or alloys and their any combination between.
• the cathode or anode can be formed by sputtering or depositing on a substrate as a corresponding material, and the substrate is a glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency.
• TFTs thin film transistors
• the organic electroluminescent device of the present application also includes other auxiliary functional regions that are favorable for carrier injection and recombination.
• the hole-transport region between the anode and the light-emitting layer, and the electron-transport region between the cathode and the light-emitting layer are favorable for carrier injection and recombination.
• the hole transport region can be a hole transport layer (HTL) with a single-layer structure, including a single-layer hole-transport layer containing only one compound and a single-layer hole-transport layer containing multiple compounds.
• the hole transport region can also be a multilayer structure including at least two layers of a hole injection layer (HIL), a hole transport layer (HTL) and an electron blocking layer (EBL).
• HIL hole injection layer
• HTL hole transport layer
• EBL electron blocking layer
• the material of the hole transport region can be selected from but not limited to phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene vinylene, polyaniline/dodeca Alkylbenzenesulfonic acid (Pani/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA ), polyaniline/poly(4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives.
• phthalocyanine derivatives such as CuPc
• conductive polymers or polymers containing conductive dopants such as polyphenylene vinylene, polyaniline/dodeca Alkylbenzenesulfonic acid (Pani/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-sty
• the material of the hole transport auxiliary layer is an aromatic amine derivative, it may be one or more of the compounds shown in HT-1 to HT-34.
• a hole injection layer is located between the anode and the hole transport layer.
• the hole injection layer can be a single compound material, or a combination of multiple compounds.
• the hole injection layer can use one or more compounds of the above-mentioned HT-1 to HT-34, or one or more compounds in the following HI1-HI3; HT-1 to HT-34 can also be used One or more compounds of doped with one or more compounds in the following HI1-HI3.
• the electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron-transport layer containing only one compound and a single-layer electron-transport layer containing multiple compounds.
• the electron transport region can also be a multilayer structure including at least two layers of electron injection layer (EIL), electron transport layer (ETL) and hole blocking layer (HBL).
• EIL electron injection layer
• ETL electron transport layer
• HBL hole blocking layer
• the electron transport layer material can be selected from, but not limited to, one or more combinations of ET-1 to ET73 listed below.
• a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer.
• the hole blocking layer can use, but is not limited to, one or more compounds of the above-mentioned ET-1 to ET-73.
• the electron injection material in the electron injection layer includes any one or a combination of at least two of the following compounds: Liq, LiF, NaCl, CsF, Li 2 O, Cs 2 CO 3 , BaO, Na, Li, Ca, Mg, Ag , Yb.
• the light extraction layer (CPL layer) can be evaporated on the cathode of the device to improve the efficiency of the device and adjust the optical microcavity.
• the thickness of each of the above-mentioned layers can adopt the conventional thickness of these layers in the art.
• the present application also provides a preparation method of the organic electroluminescent device, which comprises sequentially depositing an anode, a hole transport region, a light-emitting layer, an electron transport region and a cathode on a substrate, and then encapsulating.
• a preparation method of the organic electroluminescent device which comprises sequentially depositing an anode, a hole transport region, a light-emitting layer, an electron transport region and a cathode on a substrate, and then encapsulating.
• the method of multi-source co-evaporation is used to adjust the evaporation rate of the host material and the evaporation rate of the fluorescent dye so that the fluorescent dye reaches a preset doping ratio, and the triplet-triplet annihilation material source and
• the luminescent layer is formed by co-evaporating any one of the fluorescent dye sources mentioned above.
• the deposition methods of the anode, the hole transport region, the electron transport region and the cathode are the same as
• the organic electroluminescence device of the present application has the advantages of low driving voltage and high efficiency through the combination of specific materials in the light-emitting layer and the selection of special fluorescent dyes.
• the second aspect of the present application further provides a display device, the display device comprising the organic electroluminescence device as provided above.
• the display device may be a display device such as an OLED display, and any product or component having a display function such as a TV, a digital camera, a mobile phone, a tablet computer, etc. including the display device.
• the display device has the same advantages as that of the above-mentioned organic electroluminescent device over the prior art, which will not be repeated here.
• the hydrogen and Cl atoms between/on X 1 , X 2 , X 3 and X 4 are ortho-positioned using n-butyllithium or tert-butyllithium, etc. Metalization.
• boron tribromide is added to perform lithium-boron metal exchange
• a Bronsted base such as N,N-diisopropylethylamine is added to perform a tandem bora-Fried-Clark Futz reaction (Tandem Bora-Friedel-Crafts Reaction), and the target can be obtained.
• MALDI-TOF-MS results Molecular ion peak: 1271.55 Elemental analysis results: Theoretical value: C, 86.90; H, 7.85; B, 0.85; N, 4.41(%); Experimental value: C, 86.80; H, 7.85; B , 0.85; N, 4.51 (%).
• Synthesis of compound S-13-2 This example is basically the same as the synthesis of compound S-7-2, the difference is that in this example, S-7-1 needs to be replaced by S- 13-1.
• Target compound S-13-2 (10.38g, 92% yield, HPLC analysis purity 99.37%), white solid.
• Synthesis of compound S-52-2 This example is basically the same as the synthesis of compound S-7-2, the difference is that in this example, S-7-1 needs to be replaced by S- 52-1.
• Target compound S-52-2 (10.89 g, 86% yield, HPLC analysis purity 99.53%), white solid.
• fluorescent dyes obtained in this application were also characterized by mass spectrometry (MALDI-TOF-MS molecular ion peak), as shown in Table 1 below.
• organic electroluminescent device of the present application will be further introduced through specific examples below.
• Embodiments 1-29 respectively provide an organic electroluminescence device, and its device structure includes an anode, a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), and an emission layer (EML) in sequence. , hole blocking layer (HBL), electron transport layer (ETL), electron injection layer (EIL), cathode, and light extraction layer (CPL).
• HIL hole injection layer
• HTL hole transport layer
• EBL electron blocking layer
• EIL electron injection layer
• CPL light extraction layer
• the glass plate coated with the ITO/Ag/ITO conductive layer is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in acetone: ethanol mixed solvent, and baked in a clean environment until completely Water is removed, cleaned with UV light and ozone, and the surface is bombarded with a beam of low-energy cations;
• the hole transport layer HT-24 is vacuum evaporated on the hole injection layer, the evaporation rate is 0.1nm/s, and the total film thickness is 110nm;
• the electron blocking layer EB-1 is vacuum evaporated, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 5nm;
• the luminescent layer includes the host material BFH-4 and the fluorescent dye S-7.
• the dye is evaporated according to the doping ratio of 2%.
• the evaporation rate of the main body is 0.1nm/s, and the evaporation film thickness is 20nm.
• Yb with a thickness of 1nm is vacuum evaporated on the electron transport layer as the electron injection layer;
• the device is a top-emitting structure, including an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a cathode, and a light extraction layer from bottom to top.
• a top-emitting structure including an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a cathode, and a light extraction layer from bottom to top.
• Example 2 In the organic electroluminescent device provided in Examples 2-29, the specific preparation method is similar to that of Example 1, the difference lies in the specific selection of the host material and fluorescent dye and the mass ratio of the fluorescent dye in the light-emitting layer.
• the relevant characterization of some device fluorescent dyes in the examples is shown in Table 1 below.
• Comparative Example 1-8 provides an organic electroluminescent device, the device structure of which is consistent with that of Example 1-29, and the parameters of the corresponding functional layer are also basically the same as those of Example 1-29, the only difference being that the host material and the dye of the light-emitting layer
• the materials used in the examples are inconsistent or the doping concentration is inconsistent.
• Example 1 BFH-4 S-7, 2% 3.98V 176
• Example 2 BFH-4 S-7, 10% 3.99V 174
• Example 3 BFH-4 S-7, 15% 4.02V 170
• Example 4 BFH-4 S-7, 20% 4.02V 169
• Example 5 BFH-4 S-7, 30% 4.05V 166
• Example 6 BFH-14 S-7, 2% 3.51V 177
• Example 7 BFH-14 S-7, 15% 3.58V 171
• Example 8 BFH-14 S-7, 20% 3.59V 170
• Example 9 BFH-14 S-7, 30% 3.77V 167
• Example 10 BFH-4 S-13, 2% 3.97V 178
• Example 11 BFH-4 S-13, 15% 4.04V 173
• Example 12 BFH-4 S-24, 2% 4.03V 169
• Example 13 BFH-4 S-24, 15% 4.07V 165
• Example 14 BFH-4 S-50, 2% 3.87V 180
• Example 15 BFH-4 S-50, 15% 3.90V 175
• Example 16 BFH-4 S-52, 2% 3.88V 183
• Example 17 BFH-4 S-52, 15% 3.92V 180
• Example 18 BFH-4 S-69, 2% 3.95V 181
• Example 19 BFH-4 S-69, 15% 3.98V 179
• Example 20 BFH-4 S-146, 2% 4.05V 166
• Example 21 BFH-4 S
• the organic electroluminescent devices of Examples 1-29 of the present application by introducing a carbocyclic group or heterocyclic group represented by A covered with a large steric hindrance group into the molecular structure , can effectively reduce the driving voltage and improve the luminous efficiency;
• the organic electroluminescent device using the fluorescent dye shown in formula (1) or formula (2) in Examples 1-29 of the present application has less dependence on the mass ratio of the fluorescent dye, and with With the change of the mass ratio of the fluorescent dye concentration, the fluctuation of the driving voltage and luminous efficiency of the device is not significant; further, it can be seen from Examples 1-5 and Examples 6-9 that when the mass ratio of the fluorescent dye is between 0.5-20%, the performance of the device is more excellent;
• Comparative Examples 1-4 when ref-1 and ref-2 molecules were used as dyes, the device driving voltage and luminous efficiency were not as good as those in the examples, and when the doping concentration of the dye was changed by changing ref1 and ref2 at the same time, the device luminous efficiency and The driving voltages all have large changes; in Comparative Examples 5-8, using other types of non-triplet-triplet quenching host ref-3 and ref-4 molecules, the device driving voltage is significantly improved compared with the examples, and the luminescence The efficiency is reduced, so this application can achieve better device performance by matching a type of triplet-triplet annihilation host, which can meet the current requirements of panel manufacturers for high-performance materials, and has a good application prospect.

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