CN114551770A - Organic electroluminescent device - Google Patents
Organic electroluminescent device Download PDFInfo
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- CN114551770A CN114551770A CN202011292169.0A CN202011292169A CN114551770A CN 114551770 A CN114551770 A CN 114551770A CN 202011292169 A CN202011292169 A CN 202011292169A CN 114551770 A CN114551770 A CN 114551770A
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- 239000010410 layer Substances 0.000 claims abstract description 131
- 239000000463 material Substances 0.000 claims abstract description 42
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- 230000005525 hole transport Effects 0.000 claims abstract description 31
- 239000012044 organic layer Substances 0.000 claims abstract description 8
- -1 C2-C20 alkynyl Chemical group 0.000 claims description 132
- 125000001072 heteroaryl group Chemical group 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 44
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 238000002347 injection Methods 0.000 claims description 15
- 239000007924 injection Substances 0.000 claims description 15
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- 125000001424 substituent group Chemical group 0.000 claims description 11
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- 125000001769 aryl amino group Chemical group 0.000 claims description 8
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 6
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 6
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- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 claims description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
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- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- RHZWSUVWRRXEJF-UHFFFAOYSA-N indium tin Chemical compound [In].[Sn] RHZWSUVWRRXEJF-UHFFFAOYSA-N 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 150000002843 nonmetals Chemical class 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000005592 polycycloalkyl group Polymers 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention relates to an organic electroluminescent device which comprises a first electrode, a second electrode and an organic layer positioned between the first electrode and the second electrode, wherein the organic layer comprises a light-emitting layer, a hole transport layer and an electron transport layer, the hole transport layer comprises a compound shown in a formula (1), and the electron transport layer comprises a compound shown in a formula (2). The hole transport layer material shown in the formula (1) and the electron transport layer material shown in the formula (2) are matched for use, so that current carriers can be effectively balanced, the driving voltage of the device can be reduced, the luminous efficiency of the device is improved, and the service life of the device is prolonged.
Description
Technical Field
The present invention relates to an organic electroluminescent device, and more particularly, to an organic electroluminescent device having a low driving voltage, a high luminous efficiency, and a long lifetime.
Background
In recent years, optoelectronic devices based on organic materials have become increasingly popular. The inherent flexibility of organic materials makes them well suited for fabrication on flexible substrates, allowing for the design and production of aesthetically pleasing and crunchy optoelectronic products, with unparalleled advantages over inorganic materials. Examples of such organic optoelectronic devices include Organic Light Emitting Diodes (OLEDs), organic field effect transistors, organic photovoltaic cells, organic sensors, and the like. Among them, OLEDs are particularly rapidly developed and have been commercially successful in the field of information displays. The OLED can provide three colors of red, green and blue with high saturation, and a full-color display device manufactured by using the OLED does not need an additional backlight source and has the advantages of colorful, light, thin and soft color and the like.
As OLED products gradually enter the market, there are increasingly higher requirements on the performance of such products. People in the industry also make continuous attempts and exploration on improving the efficiency and stability of the device, wherein the mode of seeking for new materials to improve the performance of the device is more, a large number of novel materials are developed and applied to the OLED device, and although the performance of the device is improved to a certain extent, the current carrier imbalance still exists in the OLED device, so that the improvement of the efficiency and stability of the device is restricted.
The currently used OLED materials and device structures cannot completely solve the problems of OLED product efficiency, service life, cost and the like.
The present inventors have been working on developing organic functional materials, and have proposed various materials suitable for use in a hole transport layer or an electron blocking layer. Among them, chinese patent application CN111606813A has disclosed a compound having the following specific aniline structure as a hole transport layer and an electron blocking layer.
The inventor of the present invention has found through intensive research that the OLED device prepared by the above scheme has good performance of reducing voltage and prolonging the lifetime of the device, but the light emitting efficiency of the OLED device still needs to be improved, so that a scheme for matching various functional layers in the OLED device needs to be further optimized.
Disclosure of Invention
In view of the deficiencies of the prior art, it is an object of the present invention to provide an organic electroluminescent device having a lower driving voltage, and higher luminous efficiency and lifetime.
The invention provides an organic electroluminescent device, which comprises a first electrode, a second electrode and an organic layer positioned between the first electrode and the second electrode, wherein the organic layer comprises a hole transport layer, a luminescent layer and an electron transport layer, wherein the hole transport layer comprises a compound with a structure shown in a formula (1):
in the formula (1), Ar1Selected from substituted or unsubstituted C10-C50 fused ring aryl, substituted or unsubstituted C6-C50 fused ring heteroaryl;
Ar2selected from hydrogen, deuterium, halogen or one of the following substituted or unsubstituted groups: C1-C12 alkyl, C3-C30 cycloalkyl, C1-C12 alkoxy, C3-C30 cycloalkoxy, C2-C20 alkenyl, C2-C20 alkynyl, carbonyl, cyano, C6-C50 aryl, C3-C30 heteroaryl, C10-C50 fused ring aryl, and C6-C50 fused ring heteroaryl;
L1and L2Independently selected from a single bond, substituted or unsubstituted C1-C12 alkylidene, substituted or unsubstituted C6-C50 arylidene, substituted or unsubstituted C3-C30 heteroarylidene, substituted or unsubstituted C10-C50 fused ring arylidene and substituted or unsubstituted C6-C50 fused ring heteroarylidene;
G1one selected from the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, naphthyl, fluorene, spirofluorene, dibenzofuran, dibenzothiophene, dibenzoselenophene, azafluorene, azadibenzofuran, azadibenzothiophene, azadibenzoselenophene;
G2one selected from the following substituted or unsubstituted groups: C6-C50 aryl, C3-C30 heteroaryl, C10-C50 fused ring aryl and C6-C50 fused ring heteroaryl;
n is an integer of 0 to 5;
when the above groups are substituted in the formula (1), the substituent is independently selected from one of deuterium, halogen, C1-C12 alkyl, C3-C30 cycloalkyl, C1-C12 alkoxy, C3-C30 cycloalkoxy, C2-C20 alkenyl, C2-C20 alkynyl, carbonyl, cyano, C6-C50 aryl, C3-C30 heteroaryl, C10-C50 condensed ring aryl and C6-C50 condensed ring heteroaryl;
the electron transport layer comprises a compound with a structure shown as a formula (2):
in the formula (2), X1～X4Each independently is N or CR; different R is independently H, halogen, cyano, nitro, hydroxyl, C1-C12 alkyl, C1-C12 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; different R can be connected to form an aliphatic ring or an aromatic ring,
L3is a single bond, a substituted or unsubstituted aryl residue with a valence of m +1 from C6 to C60, a substituted or unsubstituted heteroaryl residue with a valence of m +1 from C3 to C60; l is4Is a single bond, a substituted or unsubstituted aryl residue with a valence of p +1 from C6 to C60, a substituted or unsubstituted heteroaryl residue with a valence of p +1 from C3 to C60;
m and p are integers of 1-3; l is3When the group is a single bond, m is 1; l is4When the group is a single bond, p is 1;
Ar3、Ar4each independently selected from H, C1-C12 alkyl, C1-C12 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, cyano or the combination thereof; ar (Ar)3、Ar4Not simultaneously being H or Ar3、Ar4Not simultaneously being C1-C12 alkyl, Ar3、Ar4Not being C1-C12 alkoxy at the same time;
in the formula (2), when the above groups are substituted, the substituents are independently selected from one or more of halogen, nitro, cyano, aryl of C6 to C60, heteroaryl of C3 to C60, alkyl of C1 to C30, alkoxy of C1 to C30, aryloxy of C6 to C60, amino, silyl of C1 to C30, arylamino of C6 to C60, heteroarylamino of C3 to C60, or a combination of at least two of them.
According to the organic electroluminescent device provided by the invention, the compound with the structure shown in the formula (1) is selected as a hole transport layer material, the compound with the structure shown in the formula (2) is selected as an electron transport layer material, and more preferably, Liq is doped as a host material in the electron transport layer as a guest material.
Preferably, in the organic electroluminescent device of the present invention, the hole transport layer comprises one or two of the following compounds:
preferably, in the organic electroluminescent device of the present invention, the electron transport layer comprises a compound having a structure represented by formula (3):
in the formula (3), R is3～R6Each independently is H, halogen, cyano, nitro, hydroxyl, alkyl of C1-C12, alkoxy of C1-C12, substituted or unsubstituted aryl of C6-C60, substituted or unsubstituted heteroaryl of C3-C60; r3～R6Can be connected to form an aliphatic ring or an aromatic ring,
L3is a single bond, a substituted or unsubstituted aryl residue with a valence of m +1 from C6 to C30, a substituted or unsubstituted heteroaryl residue with a valence of m +1 from C3 to C30; l is4Is a single bond, a substituted or unsubstituted aryl residue with a valence of p +1 from C6 to C30, a substituted or unsubstituted heteroaryl residue with a valence of p +1 from C3 to C30;
Ar3、Ar4m and p have the same meanings as defined in claim 1, and when the above groups are substituted, the substituents are independently selected from one or more of halogen, nitro, cyano, aryl of C6 to C60, heteroaryl of C3 to C60, alkyl of C1 to C30, alkoxy of C1 to C30, aryloxy of C6 to C60, amino, silyl of C1 to C30, arylamino of C6 to C60, heteroarylamino of C3 to C60;
preferably, L3And L4Not being a single bond at the same time;
further preferably, L3Is a single bond, a substituted or unsubstituted phenyl residue having a valence of m +1, a substituted or unsubstituted naphthyl residue having a valence of m +1, a substituted or unsubstituted anthracenyl residue having a valence of m +1, a substituted or unsubstituted phenanthrenyl residue having a valence of m +1, a substituted or unsubstituted pyrenyl residue having a valence of m + 1; l is4Is a single bond, a substituted or unsubstituted phenyl residue with a valence of p +1, a substituted or unsubstituted naphthyl residue with a valence of p +1, a substituted or unsubstituted anthryl residue with a valence of p +1, a substituted or unsubstituted phenanthryl residue with a valence of p +1, a substituted or unsubstituted pyrenyl residue with a valence of p + 1.
Preferably, in the formula (3), Ar3And Ar4Each independently selected from one or a combination of two or more of the following substituted or unsubstituted groups:
wherein the mark of the wavy line represents a group and L3Or L4The connecting bond of (1);
the above groups may be substituted by one or more groups selected from halogen, nitro, cyano, aryl groups of C6-C60, heteroaryl groups of C3-C60, alkyl groups of C1-C30, alkoxy groups of C1-C30, aryloxy groups of C6-C60, amino groups, silyl groups of C1-C30, arylamino groups of C6-C60, heteroarylamino groups of C3-C60, or a combination of at least two of them;
preferably, Ar is3And Ar4At least one of which is an electron deficient group.
In the present specification, the expression of Ca to Cb represents that the group has carbon atoms a to b, and the carbon atoms do not generally include the carbon atoms of the substituents unless otherwise specified. In the present invention, for the expression of chemical elements, ifUnless otherwise specified, the term "comprising isotopes of the same chemical nature, such as the expression" hydrogen ", also including the term" deuterium "or" tritium "of the same chemical nature, carbon (C) including12C、13C, etc., will not be described in detail.
In the structural formulae disclosed herein, the expression of the "-" underlined ring structure indicates that the linking site is at any position on the ring structure at which bonding can be achieved.
In the present specification, unless otherwise specified, both aryl and heteroaryl groups include monocyclic and fused rings. The monocyclic aryl group means that at least one phenyl group is contained in the molecule, and when at least two phenyl groups are contained in the molecule, the phenyl groups are independent of each other and are linked by a single bond, illustratively, a phenyl group, a biphenylyl group, a terphenylyl group, or the like; the fused ring aryl group means that at least two benzene rings are contained in the molecule, but the benzene rings are not independent of each other, but common ring sides are fused with each other, and exemplified by naphthyl, anthryl and the like; monocyclic heteroaryl means that the molecule contains at least one heteroaryl group, and when the molecule contains one heteroaryl group and other groups (e.g., aryl, heteroaryl, alkyl, etc.), the heteroaryl and other groups are independent of each other and are linked by a single bond, illustratively pyridine, furan, thiophene, etc.; fused ring heteroaryl refers to a fused ring of at least one phenyl group and at least one heteroaryl group, or, fused ring of at least two heteroaryl rings, illustratively quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, and the like
In the present specification, the substituted or unsubstituted C6 to C60 aryl group is preferably a C6 to C30 aryl group, and more preferably a group in the group consisting of phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, gronyl, perylenyl, fluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, isotridecylindenyl, spirotrimeric indenyl, and spiroisotridecylindenyl. Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl, and 4-biphenyl; terphenylThe group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracene group is selected from 1-anthracene group, 2-anthracene group and 9-anthracene group; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracene group is selected from the group consisting of 1-tetracene, 2-tetracene, and 9-tetracene. Preferred examples of the aryl group in the present invention include phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof, anthryl, triphenylenyl, pyrenyl, perylenyl, perylene, and the like,
A group of the group consisting of a phenyl group and a tetracenyl group. The biphenyl group is selected from the group consisting of 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracene group is selected from the group consisting of 1-anthracene group, 2-anthracene group, and 9-anthracene group; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9, 9-dimethylfluorene, 9-spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracene group is selected from the group consisting of 1-tetracene, 2-tetracene, and 9-tetracene. The aryl group having C6 to C60 in the present invention may be a group in which the above groups are bonded by a single bond or/and condensed.
Specific examples of the m + 1-valent and p + 1-valent aryl residues in the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned aryl residues.
The heteroatom in the present invention is generally referred to as being selected from N, O, S, P, Si and Se, preferably from N, O, S.
In the present specification, the substituted or unsubstituted C3 to C60 heteroaryl group is preferably a C3 to C30 heteroaryl group, more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, and the like, and specific examples thereof include: furyl, thienyl, pyrrolyl, pyridyl, benzofuryl, benzothienyl, isobenzofuryl, isobenzothienyl, indolyl, isoindolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalimidazolyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzpyridazinyl, Pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazananthracenyl, 2, 7-diazpyrenyl, 2, 3-diazpyrenyl, 1, 6-diazenyl, 1, 8-diazenyl, 4, 5, 9, 10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, 1, 2, 3-triazolyl, 1, 2, 4-triazolyl, benzotriazolyl, 1, 2, 3-oxadiazolyl, 1, 2, 4-oxadiazolyl, 1, 2, 5-oxadiazolyl, 1, 2, 3-thiadiazolyl, 1, 2, 4-thiadiazolyl, 1, 2, 5-thiadiazolyl, 1, 3, 4-thiadiazolyl, 1, 3, 5-triazinyl, 1, 2, 4-triazinyl, 1, 2, 3-triazinyl, tetrazolyl, 1, 2, 4, 5-tetrazinyl, 1, 2, 3, 4-tetrazinyl, 1, 2, 3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazole, and the like. Preferred examples of the heteroaryl group in the present invention include furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole or indolocarbazole. The heteroaryl group having C3-C60 in the present invention may be a group in which the above groups are bonded by a single bond or/and condensed.
Specific examples of the heteroaryl residue having a valence of m +1 and a valence of p +1 in the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned examples of the heteroaryl group.
In the present specification, alkyl includes the concept of cycloalkyl. Examples of the C1-C30 alkyl group include: 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, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2, 2, 2-trifluoroethyl and the like.
In the present specification, cycloalkyl includes monocycloalkyl and polycycloalkyl groups, and may be, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
In the present specification, examples of the C1 to C30 alkoxy group include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like, among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy, more preferably methoxy.
Examples of the C1-C30 silyl group in the present specification include silyl groups substituted with the groups exemplified for the C1-C30 alkyl groups, and specifically include: methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, t-butyldimethylsilyl, t-butyldiphenylsilyl and the like.
In the present specification, examples of the halogen include: fluorine, chlorine, bromine, iodine, and the like.
More specifically, R is the above-mentioned3～R6Preferable examples of the group of (1) include hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and 2-methylPhenylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2, 2, 2-trifluoroethyl, phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, bornyl, perylenyl, fluoresceryl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, triindenyl, isotridecyl, spirotrimeric indenyl, spiroisotridecyl, furanyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, terphenylyl, terphenylenyl, pyrenylethyl, terphenylenyl, phenanthrenyl, terphenylenyl, pentacenyl, terphenylyl, terphenylenyl, furyl, cumenyl, etc, Pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazahrenyl, 2, 7-diazapyryl, 2, 3-diazapyryl, 1, 6-diazapyryl, 1, 8-diazenyl, 4, 5, 9, 10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, 1, 2, 3-triazolyl, 1, 2, 4-triazolyl, benzotriazolyl, 1, 2, 3-oxadiazolyl, 1, 2, 4-oxadiazolyl, 1, 2, 5-oxadiazolyl, 1, 2, 3-thiadiazolyl, 1, 2, 4-thiadiazolyl, 1, 2, 5-thiadiazolyl, 1, 3, 4-thiadiazolyl, 1, 3, 5-triazinyl, 1, 2, 4-triazinyl, 1, 2, 3-triazinyl, tetrazolyl, 1, 2, 4, 5-tetrazinyl, 1, 2, 3, 4-tetrazinyl, 1, 2, 3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolylOr a combination of two selected from the above. But R is3～R6These groups are not limited.
Ar3、Ar4Independently selected from C1-C12 alkyl, C1-C12 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, cyano or combinations thereof, refers to groups obtained by single bond connection or fused connection of the above-exemplified groups.
In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or a plurality of substituents, and when a plurality of substituents are present, different substituents may be selected from the group.
Further, Ar3And Ar4When at least one of the groups is an electron-deficient group, the technical effect of the present invention is more excellent. The term "electron-deficient group" means a group in which the electron cloud density on the benzene ring is reduced by substituting hydrogen on the benzene ring with the group, and usually such a group has a Hammett value of more than 0.6. The Hammett value is a representation of the charge affinity for a particular group and is a measure of the electron withdrawing group (positive Hammett value) or electron donating group (negative Hammett value). The Hammett equation is described In more detail In Thomas H.Lowry and Kathelen Schueler Richardson, "mechanics and Theory In Organic Chemistry", New York,1987, 143-. Such groups may be listed but are not limited to: triazinyl, pyrimidinyl, benzopyrimidinyl, benzopyridyl, naphthyridinyl, phenanthridinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, pyridazinyl, and alkyl-or aryl-substituted groups of the foregoing, such groups being preferably triazine, pyrimidine, arylcyano, pyridine, quinazoline and the like.
Preferably, in the organic electroluminescent device of the present invention, the electron transport layer comprises compounds having structures represented by formulas (III-1) to (III-8):
in the formula, R3～R6The same as the meaning expressed in claim 3;
y is C, N, O or S; x is a single bond, C, N, O or S;
Z1～Z6each independently is N or CR, said R, R7～R10Each independently is one or a combination of at least two of halogen, nitryl, cyano, aryl of C6-C60, heteroaryl of C3-C60, alkyl of C1-C30, alkoxy of C1-C30, aryloxy of C6-C60, amino, silyl of C1-C30, arylamino of C6-C60 and heteroarylamino of C3-C60.
Preferably, in the organic electroluminescent device of the present invention, the electron transport layer comprises one or two of the following compounds:
preferably, in the organic electroluminescent device of the present invention, the hole transport layer has a thickness of 1nm to 150nm, for example, 50nm, 70nm, 80nm, 90nm, 110nm, 130nm, 150nm, etc., preferably 70nm to 90 nm.
Preferably, in the organic electroluminescent device of the present invention, the thickness of the electron transport layer is 10nm to 50nm, for example, 10nm, 15nm, 20nm, 25nm, 30nm, 40nm, 50nm, etc., preferably 20nm to 30 nm.
Preferably, in the organic electroluminescent device of the present invention, the compound having the structure represented by formula (2) contained in the electron transport layer is used as a host material in the electron transport layer, and Liq is also contained as a guest material in the electron transport layer. The doping ratio of the guest material in the host material in the electron transport layer is 10% to 200% (molar ratio), for example, 10%, 50%, 100%, 120%, 150%, 200%, etc., preferably 50% to 150% (molar ratio).
In the organic electroluminescent device of the present invention, the organic layer further includes at least one of a hole injection layer, a hole blocking layer, an electron injection layer, and an electron blocking layer.
The organic electroluminescent device is prepared by adopting a vacuum deposition mode, and can also be prepared by adopting other modes, and is not limited to vacuum deposition. The invention is illustrated with a device prepared by vacuum deposition.
The preparation method comprises the steps of cleaning a substrate, drying, pretreating, putting the substrate into a cavity, and sequentially carrying out vacuum deposition on a hole injection layer, a hole transport layer, a luminescent layer, an electron transport layer, an electron injection layer and a cathode.
The substrate is a rigid substrate or a flexible substrate, the rigid substrate comprises a glass substrate, a Si substrate and the like, and the flexible substrate comprises a polyvinyl alcohol (PVA) film, a Polyimide (PD) film, a Polyester (PET) film and the like; the substrate of the present invention is preferably a rigid glass substrate.
The anode may preferably be a conductive compound, alloy, metal or mixture of such materials having a large work function. Inorganic materials may be used, including metals or metal oxides, laminates of metals and metals or metals and non-metals, and the like, the metal oxides including Indium Tin Oxide (ITO), zinc oxide (ZnO), Indium Zinc Oxide (IZO), tin oxide (SnO), and the like, and the metals including gold, silver, copper, aluminum, and the like, which have a high work function; ITO is preferred as the anode of the present invention.
The hole injection layer is formed by doping 6% of f4-TCNQ with m-MTDATA, and the structure is as follows:
the host material of the blue light emitting layer is selected from any one or at least two combinations of the following compounds represented by BFH-1 to BFH-17:
the guest material of the blue light emitting layer is selected from any one or at least two combinations of the following compounds represented by BFD-1 to BFD-24:
the host material of the phosphorescent light-emitting layer is selected from any one or at least two combinations of compounds shown as the following PH-1 to PH-85:
the phosphorescent light-emitting layer guest material is selected from any one or at least two combinations of the following compounds represented by GPD-1 to GPD-47 or any one or at least two combinations of the compounds represented by RPD-1 to RPD-28:
the guest doping material of the electron transport layer is Liq, and the structural formula of the guest doping material is as follows:
the cathode is magnesium silver mixture, metal such as LiF/Al, ITO, etc., metal mixture, oxide, etc., and Yb/magnesium silver mixture is preferred in the invention.
Compared with the prior art, the organic electroluminescent device provided by the invention has the advantages of reducing the driving voltage of the device, improving the luminous efficiency, prolonging the service life of the device and the like.
Drawings
Fig. 1 is a schematic structural view of an organic electroluminescent device provided in embodiment 1 of the present invention;
the organic electroluminescent material comprises a substrate, a light-emitting layer, a cathode, an anode, a cathode, a luminescent layer, a cathode, and a luminescent layer, wherein the anode is 1-anode, the hole injection layer is 2-hole injection layer, the hole transport layer is 3-hole transport layer, the light-emitting layer is 4-light emitting layer, the electron transport layer is 5-electron injection layer, and the cathode is 7-cathode.
Detailed Description
For the purpose of facilitating an understanding of the present invention, the following examples are set forth herein. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
The compound having the structure represented by the general formula (1) in the present invention can be produced according to the method disclosed in patent application CN 111606813A.
The compound of the above-described structure represented by the general formula (2) in the present invention can be produced according to the method described in patent application No. 202011092633.1. The preparation method of the invention is not described in detail.
Example 1
An embodiment of the present invention provides an organic electroluminescent device, which has a structure shown in fig. 1 in the specification, and specifically includes an anode 1, a hole injection layer (HIL layer) 2, a hole transport layer (HTL layer) 3, an emission layer (EML layer) 4, an electron transport layer (ETL layer) 5, an electron injection layer (EIL layer) 6, and a cathode 7.
The preparation method of the organic electroluminescent device comprises the following steps:
on an anode glass substrate having a film thickness of 150nm and formed with Indium Tin Oxide (ITO)/Ag/Indium Tin Oxide (ITO), a vacuum deposition method was used to obtain a film having a vacuum degree of 2X 10-4And depositing each film layer under Pa. Firstly, forming an m-MTDATA: 6% f4-TCNQ film as a hole injection layer (6% refers to the doping proportion of f-4TCNQ in the hole injection layer) on ITO, wherein the evaporation rate ratio of the m-MTDATA to the f4-TCNQ is 1:0.06, the evaporation rate of the m-MTDATA is 1 angstrom/second, and the total thickness is 100 nm; then 80nm of C4 was deposited as a hole transport layer at an evaporation rate of 1A/s. Evaporating on the hole transport layer, and evaporating blue light host BFH-1 and 3% object BFD-1 (3% refers to the doping proportion of an object material in the light-emitting layer) from different evaporation sources to serve as a blue light-emitting layer (B-EML layer) together, wherein the evaporation rate ratio is 1:0.03, the evaporation rate of BFH-1 is 1 angstrom/second, and the thickness of the blue light-emitting layer is 20 nm; d27 with the thickness of 25nm, namely 100 percent Liq (100 percent refers to the doping molar ratio of Liq serving as a guest material in the electron transport layer in a host material D27) is deposited to serve as the electron transport layer, and the evaporation rates of D27 and Liq are both 1 angstrom/second; then depositing 1nm LiF as an electron injection layer, wherein the evaporation rate is 0.1 angstrom/second; an Al layer with a thickness of 150nm was used as the cathode of the device.
Example 2
The only difference from example 1 is that the evaporated thickness of the hole transport layer material C4 was 50 nm.
Example 3
The only difference from example 1 is that the evaporated thickness of the hole transport layer material C4 was 70 nm.
Example 4
The only difference from example 1 is that the evaporated thickness of the hole transport layer material C4 was 90 nm.
Example 5
The only difference from example 1 is that the evaporated thickness of the hole transport layer material C4 was 110 nm.
Example 6
The only difference from example 1 is that the evaporated thickness of the hole transport layer material C4 was 130 nm.
Example 7
The only difference from example 1 is that the evaporated thickness of the hole transport layer material C4 was 150 nm.
Example 8
The only difference from example 1 is that the electron transport layer has a vapor deposition thickness of 10 nm.
Example 9
The only difference from example 1 is that the electron transport layer has an evaporation thickness of 15 nm.
Example 10
The only difference from example 1 is that the electron transport layer has a vapor deposition thickness of 20 nm.
Example 11
The only difference from example 1 is that the electron transport layer had a vapor deposition thickness of 30 nm.
Example 12
The only difference from example 1 is that the electron transport layer has a vapor deposition thickness of 40 nm.
Example 13
The only difference from example 1 is that the electron transport layer has a deposition thickness of 50 nm.
Example 14
The difference from example 1 is only that the doping ratio of the guest of the electron transport layer in the host is adjusted to 10%.
Example 15
The only difference from example 1 is that the doping ratio of the electron transport layer guest in the host is adjusted to 50%.
Example 16
The difference from example 1 is only that the doping ratio of the guest of the electron transport layer in the host is adjusted to 120%.
Example 17
The difference from example 1 is only that the doping ratio of the guest of the electron transport layer in the host is adjusted to 150%.
Example 18
The difference from example 1 is only that the doping ratio of the guest of the electron transport layer in the host is adjusted to 200%.
Example 19
The only difference from example 1 was that the hole transport layer material C4 was replaced with C4+ C169.
Example 20
The only difference from example 1 was that the electron transport layer host material D27 was replaced with D27+ D122.
Example 21
The difference from example 1 is only that the light emitting layer is prepared as a red light emitting layer (R-EML), that is, the light emitting layer preparation method is replaced by evaporating 40nm red host PH-4 and red dye RPD-2, and the dye doping ratio is 3%.
Example 22
The difference from example 1 is only that the light emitting layer was prepared as a green light emitting layer (G-EML), that is, the light emitting layer preparation method was replaced with evaporation of 35nm of green host PH-15 and green dye GPD-27 with a dye doping ratio of 10%.
Comparative example 1
The only difference from example 1 is that the hole transport layer C4 was replaced with the compound HT-4:
comparative example 2
The only difference from example 1 is that compound D27 of the invention was replaced by compound ET-19:
comparative example 3
The only difference from example 1 was that the hole transport layer C4 was replaced with compound HT-4 and the electron transport layer compound D27 was replaced with compound ET-19.
Comparative example 4
The difference from the comparative example 3 is only that the luminescent layer is replaced by evaporating 40nm red host PH-4 and red dye RPD-2, and the dye doping ratio is 3%.
Comparative example 5
The difference from the embodiment 3 is only that the luminescent layer is replaced by evaporating 35nm green host PH-15 and green dye GPD-27, and the dye doping ratio is 10%.
Performance testing
(1) The organic electroluminescent devices prepared in examples and comparative examples were measured for driving voltage and current efficiency and lifetime of the devices at the same brightness. Specifically, the luminance of the organic electroluminescent device was measured at 1000cd/m blue light as the voltage was boosted at a rate of 0.1V per second2Green light 10000cd/m2Red light 3000cd/m2The voltage is the driving voltage (V), and the current density at the moment is measured; the ratio of brightness to current density is the current efficiency (CE, cd/A);
(2) the life test of LT97 is as follows: at 400A/m2The green light is 400A/m2At the red light of 600A/m2Next, the time, in hours, at which the luminance of the organic electroluminescent device was decreased to 97% of the initial luminance was measured while maintaining a constant current.
The test results are shown in table 1.
Table 1;
as can be seen from table 1, the blue light device (examples 1 to 20), the red light device (example 21) and the green light device (example 22) are respectively prepared by using the compound of formula (1) as a hole transport layer material and the compound of formula (2) as an electron transport layer material in combination and matching, and compared with the blue light device, the red light device and the green light device prepared by using the hole transport layer material and the electron transport layer material matching schemes of the prior art materials in comparative examples 1 to 5, the examples 1 to 22 of the present invention relatively achieve the reduction of the driving voltage of the devices, the improvement of the current efficiency of the devices, and the significant improvement of the lifetime of the devices, thereby generally and effectively improving the performance of the OLED display device.
The applicant states that the present invention is illustrated by the above examples to show the detailed process equipment and process flow of the present invention, but the present invention is not limited to the above detailed process equipment and process flow, i.e. it does not mean that the present invention must rely on the above detailed process equipment and process flow to be implemented. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (10)
1. An organic electroluminescent device comprises a first electrode, a second electrode and an organic layer positioned between the first electrode and the second electrode, wherein the organic layer comprises a hole transport layer, a luminescent layer and an electron transport layer, and the hole transport layer comprises a compound with a structure shown in a formula (1):
in the formula (1), the reaction mixture is,Ar1selected from substituted or unsubstituted C10-C50 fused ring aryl, substituted or unsubstituted C6-C50 fused ring heteroaryl;
Ar2selected from hydrogen, deuterium, halogen or one of the following substituted or unsubstituted groups: C1-C12 alkyl, C3-C30 cycloalkyl, C1-C12 alkoxy, C3-C30 cycloalkoxy, C2-C20 alkenyl, C2-C20 alkynyl, carbonyl, cyano, C6-C50 aryl and C3-C30 heteroaryl;
L1and L2Independently selected from a single bond, substituted or unsubstituted C1-C12 alkylene, substituted or unsubstituted C6-C50 arylene, and substituted or unsubstituted C3-C30 heteroarylene;
G1one selected from the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, naphthyl, fluorene, spirofluorene, dibenzofuran, dibenzothiophene, dibenzoselenophene, azafluorene, azadibenzofuran, azadibenzothiophene, azadibenzoselenophene;
G2one selected from the following substituted or unsubstituted groups: C6-C50 aryl, C3-C30 heteroaryl;
n is an integer of 0 to 5;
when the above groups are substituted in the formula (1), the substituent is independently selected from one of deuterium, halogen, C1-C12 alkyl, C3-C30 cycloalkyl, C1-C12 alkoxy, C3-C30 cycloalkoxy, C2-C20 alkenyl, C2-C20 alkynyl, carbonyl, cyano, C6-C50 aryl, C3-C30 heteroaryl, C10-C50 condensed ring aryl and C6-C50 condensed ring heteroaryl;
the electron transport layer comprises a compound with a structure shown as a formula (2):
in the formula (2), X1～X4Each independently is N or CR; different R is independently H, halogen, cyano, nitro, hydroxyl, C1-C12 alkyl, C1-C12 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstitutedA heteroaryl group of C3 to C60; different R can be connected to form an aliphatic ring or an aromatic ring,
L3is a single bond, a substituted or unsubstituted aryl residue with a valence of m +1 from C6 to C60, a substituted or unsubstituted heteroaryl residue with a valence of m +1 from C3 to C60; l is4Is a single bond, a substituted or unsubstituted aryl residue with a valence of p +1 from C6 to C60, a substituted or unsubstituted heteroaryl residue with a valence of p +1 from C3 to C60;
m and p are integers of 1-3; l is3When the group is a single bond, m is 1; l is4When the group is a single bond, p is 1;
Ar3、Ar4each independently selected from H, C1-C12 alkyl, C1-C12 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, cyano or the combination thereof; ar (Ar)3、Ar4Not simultaneously being H or Ar3、Ar4Not simultaneously being C1-C12 alkyl, Ar3、Ar4Not being C1-C12 alkoxy at the same time;
in the formula (2), when the above groups are substituted, the substituents are independently selected from one or more of halogen, nitro, cyano, aryl of C6 to C60, heteroaryl of C3 to C60, alkyl of C1 to C30, alkoxy of C1 to C30, aryloxy of C6 to C60, amino, silyl of C1 to C30, arylamino of C6 to C60, heteroarylamino of C3 to C60, or a combination of at least two of them.
2. The organic electroluminescent device according to claim 1, wherein the hole transport layer comprises one or both of the following compounds:
3. the organic electroluminescent device according to claim 1, wherein the electron transport layer comprises a compound having a structure represented by formula (3):
in the formula (3), R is3～R6Each independently is H, halogen, cyano, nitro, hydroxyl, alkyl of C1-C12, alkoxy of C1-C12, substituted or unsubstituted aryl of C6-C60, substituted or unsubstituted heteroaryl of C3-C60; r3～R6Can be connected to form an aliphatic ring or an aromatic ring,
L3is a single bond, a substituted or unsubstituted aryl residue with a valence of m +1 from C6 to C30, a substituted or unsubstituted heteroaryl residue with a valence of m +1 from C3 to C30; l is4Is a single bond, a substituted or unsubstituted aryl residue with a valence of p +1 from C6 to C30, a substituted or unsubstituted heteroaryl residue with a valence of p +1 from C3 to C30;
Ar3、Ar4m and p have the same meanings as defined in claim 1, and when the above groups are substituted, the substituents are independently selected from one or more of halogen, nitro, cyano, aryl of C6 to C60, heteroaryl of C3 to C60, alkyl of C1 to C30, alkoxy of C1 to C30, aryloxy of C6 to C60, amino, silyl of C1 to C30, arylamino of C6 to C60, heteroarylamino of C3 to C60;
preferably, L3And L4Not being a single bond at the same time;
further preferably, L3Is a single bond, a substituted or unsubstituted phenyl residue having a valence of m +1, a substituted or unsubstituted naphthyl residue having a valence of m +1, a substituted or unsubstituted anthracenyl residue having a valence of m +1, a substituted or unsubstituted phenanthrenyl residue having a valence of m +1, a substituted or unsubstituted pyrenyl residue having a valence of m + 1; l is4Is a single bond, a substituted or unsubstituted phenyl residue with a valence of p +1, a substituted or unsubstituted naphthyl residue with a valence of p +1, a substituted or unsubstituted anthryl residue with a valence of p +1, a substituted or unsubstituted phenanthryl residue with a valence of p +1, a substituted or unsubstituted pyrenyl residue with a valence of p + 1.
4. The organic electroluminescent device according to claim 1 or 3, wherein Ar is Ar3And Ar4Each independently selected from one or two or more of the following substituted or unsubstituted groupsThe combination of (A) and (B):
wherein the mark of the wavy line represents a group and L3Or L4The connecting bond of (1);
the above groups may be substituted by one or more groups selected from halogen, nitro, cyano, aryl groups of C6-C60, heteroaryl groups of C3-C60, alkyl groups of C1-C30, alkoxy groups of C1-C30, aryloxy groups of C6-C60, amino groups, silyl groups of C1-C30, arylamino groups of C6-C60, heteroarylamino groups of C3-C60, or a combination of at least two of them;
preferably, Ar is3And Ar4At least one of which is an electron deficient group.
5. The organic electroluminescent device according to claim 1, wherein the electron transport layer comprises compounds having structures represented by formulas (III-1) to (III-8):
in the formula, R3～R6The same as the meaning expressed in claim 3;
y is C, N, O or S; x is a single bond, C, N, O or S;
Z1～Z6each independently is N or CR, said R, R7～R10Each independently is one or at least two of halogen, nitryl, cyano, aryl of C6-C60, heteroaryl of C3-C60, alkyl of C1-C30, alkoxy of C1-C30, aryloxy of C6-C60, amino, silyl of C1-C30, arylamino of C6-C60 and heteroarylamino of C3-C60And (4) combining.
6. The organic electroluminescent device according to claim 1, wherein the electron transport layer comprises one or both of the following compounds:
7. the organic electroluminescent device according to any one of claims 1 to 6, wherein the hole transport layer has a thickness of 1nm to 150 nm;
preferably, the thickness of the hole transport layer is 70nm to 90 nm.
8. The organic electroluminescent device according to any one of claims 1 to 6, wherein the thickness of the electron transport layer is 10nm to 50 nm;
preferably, the thickness of the electron transport layer is 20nm to 30 nm.
9. The organic electroluminescent device according to claim 1, wherein the doping ratio of the guest material in the electron transport layer in the host material is 10% to 200%;
more preferably, the doping ratio of the guest material in the electron transport layer in the host material is 50% to 150%.
10. The organic electroluminescent device according to claim 1, wherein the organic layer further comprises at least one of a hole injection layer, a hole blocking layer, an electron injection layer, and an electron blocking layer.
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| KR20160012066A (en) * | 2014-07-22 | 2016-02-02 | 삼성디스플레이 주식회사 | Organic light-emitting device |
| CN109360905A (en) * | 2018-09-11 | 2019-02-19 | 长春海谱润斯科技有限公司 | A kind of organic electroluminescence device |
| CN109906225A (en) * | 2016-10-27 | 2019-06-18 | 株式会社斗山 | Organic compound and organic electroluminescent device comprising it |
| CN111211235A (en) * | 2018-11-22 | 2020-05-29 | 固安鼎材科技有限公司 | Organic electroluminescent device |
| CN111606813A (en) * | 2019-02-25 | 2020-09-01 | 北京鼎材科技有限公司 | Compound, organic electronic light-emitting device comprising same and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160012066A (en) * | 2014-07-22 | 2016-02-02 | 삼성디스플레이 주식회사 | Organic light-emitting device |
| CN109906225A (en) * | 2016-10-27 | 2019-06-18 | 株式会社斗山 | Organic compound and organic electroluminescent device comprising it |
| CN109360905A (en) * | 2018-09-11 | 2019-02-19 | 长春海谱润斯科技有限公司 | A kind of organic electroluminescence device |
| CN111211235A (en) * | 2018-11-22 | 2020-05-29 | 固安鼎材科技有限公司 | Organic electroluminescent device |
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