CN114075204B - Phosphorescent host material, phosphorescent host material composition, organic electroluminescent device and electronic device - Google Patents
Phosphorescent host material, phosphorescent host material composition, organic electroluminescent device and electronic device Download PDFInfo
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- CN114075204B CN114075204B CN202110869242.4A CN202110869242A CN114075204B CN 114075204 B CN114075204 B CN 114075204B CN 202110869242 A CN202110869242 A CN 202110869242A CN 114075204 B CN114075204 B CN 114075204B
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- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- UFQGSPKFLBLFAY-UHFFFAOYSA-N cyclohexane cyclopentane Chemical compound C1CCCCC1.C1CCCCC1.C1CCCC1 UFQGSPKFLBLFAY-UHFFFAOYSA-N 0.000 description 1
- 125000005345 deuteroalkyl group Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 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
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- FQKSBRCHLNOAGY-UHFFFAOYSA-N indolo[2,3-a]carbazole Chemical compound C1=CC=C2N=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 FQKSBRCHLNOAGY-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 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
- 238000001953 recrystallisation Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 125000005760 substituted naphthylene group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000005106 triarylsilyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
Classifications
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Abstract
The application provides a phosphorescent host material and a composition thereof, an organic electroluminescent device and an electronic device, and belongs to the field of organic electroluminescence. The structure of the phosphorescence host material is shown in the formula 1, and the phosphorescence host material is applied to an organic electroluminescent device, so that the performance of the organic electroluminescent device can be obviously improved.
Description
Technical Field
The application relates to the technical field of organic electroluminescence, in particular to a phosphorescent main body material and a composition thereof, an organic electroluminescent device and an electronic device.
Background
As a new generation display technology, the organic electroluminescent material (OLED) has the advantages of ultra-thin, self-luminescence, wide viewing angle, quick response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, low energy consumption and the like, and is widely applied to industries of flat panel display, flexible display, solid-state lighting, vehicle-mounted display and the like.
Currently, phosphorescent organic electroluminescent devices are a major development direction for green organic electroluminescent devices, and are mainly used for display devices such as mobile phones, vehicles, and the like. However, with respect to the green organic electroluminescent device, there remain problems of reduced luminous efficiency, shortened lifetime, and the like, thereby resulting in reduced device performance. Therefore, phosphorescent host materials have to solve these efficiency or lifetime problems, and there is a continuous need to develop new materials for organic light emitting devices that are highly efficient, long-lived, and suitable for mass production.
It should be noted that the information disclosed in the above background section is only for enhancing understanding of the background of the application and thus may include information that does not form the prior art that is already known to those of ordinary skill in the art.
Disclosure of Invention
The application provides a phosphorescent host material and a phosphorescent host composition, an organic electroluminescent device and an electronic device, which are used for solving the problems of low luminous efficiency and shortened service life in the prior art.
In order to achieve the above purpose, the present application adopts the following technical scheme:
according to a first aspect of the present application, there is provided a phosphorescent host material having a structure as shown in formula 1:
wherein each R 1 、R 2 Or R is 3 Each independently selected from deuterium, halogen group, cyano, aryl group of 6-12 carbon atoms, heteroaryl group of 5-12 carbon atoms, alkyl group of 1-5 carbon atoms, haloalkyl group of 1-5 carbon atoms, cycloalkyl group of 3-10 carbon atoms;
n 1 represents a substituent R 1 Number n of (n) 1 Selected from 0, 1, 2 or 3, when n 1 When the number is greater than 1, any two R 1 The same or different;
n 2 represents a substituent R 2 Number n of (n) 2 Selected from 0, 1 or 2, when n 2 When the number is greater than 1, any two R 2 The same or different;
n 3 represents a substituent R 3 Number n of (n) 3 Selected from 0, 1, 2, 3 or 4, when n 3 When the number is greater than 1, any two R 3 The same or different;
L、L 1 、L 2 each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms;
Ar 1 、Ar 2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms;
a. b is independently selected from 0, 1, 2, 3, 4 or 5, and a+b is more than or equal to 1;
said L, L 1 、L 2 、Ar 1 、Ar 2 The substituents in (a) are independently selected fromFrom deuterium, halogen group, cyano group, heteroaryl group having 3 to 12 carbon atoms, aryl group having 6 to 12 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, heterocycloalkyl group having 2 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms;
optionally in Ar 1 、Ar 2 Any two adjacent substituents form a ring.
The phosphorescent host material provided by the application adopts indolocarbazole in a specific condensed mode and combines with triazine groups, so that the material has a higher T1 energy level (triplet energy level) and balances the hole and electron transmission characteristics. The fluorine-substituted diphenyl benzene structure is formed by introducing the fluorine-substituted phenyl structure on indolocarbazole to be connected with biphenyl, and the electron injection characteristic of the material can be obviously improved on the premise of not influencing the energy level T1, so that the exciton recombination efficiency is further improved. When the phosphorescence host material is used for an organic light-emitting layer of a green organic electroluminescent device, the performance of the organic electroluminescent device can be effectively improved.
A second aspect of the present application provides a composition for a light emitting layer of an organic phosphorescent light emitting device, the composition comprising the phosphorescent host material of the first aspect.
A third aspect of the present application provides an organic electroluminescent device comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the phosphorescent host material of the first aspect or the composition for the light-emitting layer of the organic phosphorescent light-emitting device of the second aspect.
A fourth aspect of the application provides an electronic device comprising the electronic component of the third aspect.
Drawings
The accompanying drawings, which are incorporated in and constitute a part of this specification, illustrate embodiments consistent with the application and together with the description, serve to explain the principles of the application.
Fig. 1 is a schematic structural view of an organic electroluminescent device of the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the application.
Description of the reference numerals
100. An anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 321. a hole transport layer; 322. a hole assist layer; 330. an organic light emitting layer; 340. a hole blocking layer; 350. an electron transport layer; 360. an electron injection layer; 400. an electronic device.
Specific embodiments of the present application have been shown by way of the above drawings and will be described in more detail below. The drawings and the written description are not intended to limit the scope of the inventive concepts in any way, but rather to illustrate the inventive concepts to those skilled in the art by reference to the specific embodiments.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments may be embodied in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the example embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application.
In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals in the drawings denote the same or similar structures, and thus detailed descriptions thereof will be omitted.
The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application. One skilled in the relevant art will recognize, however, that the inventive aspects may be practiced without one or more of the specific details, or with other methods, components, materials, etc. In other instances, well-known structures, materials, or operations are not shown or described in detail to avoid obscuring the main technical idea of the application.
The application provides a phosphorescence host material, the structure of which is shown in formula 1:
wherein each R 1 、R 2 Or R is 3 Each independently selected from deuterium, halogen group, cyano, aryl group of 6-12 carbon atoms, heteroaryl group of 5-12 carbon atoms, alkyl group of 1-5 carbon atoms, haloalkyl group of 1-5 carbon atoms, cycloalkyl group of 3-10 carbon atoms;
n 1 represents a substituent R 1 Number n of (n) 1 Selected from 0, 1, 2 or 3, when n 1 When the number is greater than 1, any two R 1 The same or different;
n 2 represents a substituent R 2 Number n of (n) 2 Selected from 0, 1 or 2, when n 2 When the number is greater than 1, any two R 2 The same or different;
n 3 represents a substituent R 3 Number n of (n) 3 Selected from 0, 1, 2, 3 or 4, when n 3 When the number is greater than 1, any two R 3 The same or different;
L、L 1 、L 2 each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms;
Ar 1 、Ar 2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms;
a. b is independently selected from 0, 1, 2, 3, 4 or 5, and a+b is more than or equal to 1;
said L, L 1 、L 2 、Ar 1 、Ar 2 The substituents of (a) are each independently selected from deuterium, halogen group, cyano group, heteroaryl group having 3-12 carbon atoms, aryl group having 6-12 carbon atoms, trialkylsilyl group having 3-12 carbon atoms, alkyl group having 1-10 carbon atoms, haloalkyl group having 1-10 carbon atoms, and carbon atom Cycloalkyl of 3 to 10, heterocycloalkyl of 2 to 10 carbon atoms, and alkoxy of 1 to 10 carbon atoms;
optionally in Ar 1 、Ar 2 Any two adjacent substituents form a ring.
In the present application, the description modes "each independently selected from" and "each independently selected from" are used interchangeably, and should be understood in a broad sense, which may mean that specific options expressed between the same symbols in different groups do not affect each other, or that specific options expressed between the same symbols in the same groups do not affect each other. For example, the number of the cells to be processed,wherein each q is independently 0, 1, 2 or 3, and each R "is independently selected from hydrogen, deuterium, fluorine, chlorine", with the meaning: the formula Q-1 represents Q substituent groups R ' on the benzene ring, wherein R ' can be the same or different, and the options of each R ' are not mutually influenced; the formula Q-2 represents that each benzene ring of the biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced each other.
In the present application, such terms as "substituted or unsubstituted" mean that the functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl or unsubstituted aryl having a substituent Rc. Wherein Rc, the substituent mentioned above, may be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuteroalkyl group having 1 to 10 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms.
In the present application, the "substituted" functional group may be substituted with one or more substituents of Rc described above; when two substituents Rc are attached to the same atom, the two substituents Rc may be present independently or attached to each other to form a ring with the atom; when two adjacent substituents Rc are present on a functional group, the adjacent two substituents Rc may be present independently or fused to the functional group to which they are attached to form a ring.
In the present application, the terms "optional", "optionally" and "optionally" mean that the subsequently described event may, but need not, occur, and that the description includes instances where the event occurs or does not. For example, "optionally, two adjacent substituents are x to form a ring; by "is meant that the two substituents may form a ring but do not necessarily form a ring, including: a scenario in which two adjacent substituents form a ring and a scenario in which two adjacent substituents do not form a ring.
In the present application, "any two adjacent substituents form a ring", and "any two adjacent substituents" may include two substituents on the same atom, and may include two adjacent atoms each having one substituent; wherein when two substituents are present on the same atom, the two substituents may form a saturated or unsaturated ring with the atom to which they are commonly attached; when two adjacent atoms each have a substituent, the two substituents may be fused into a ring. For example, when Ar 1 When there are 2 or more substituents and any adjacent substituents form a ring, the ring formed is a saturated ring or an unsaturated ring, and the number of carbon atoms is 5 to 13, for example: fluorene ring, benzene ring, naphthalene ring, cyclopentane, cyclohexane, adamantane, and the like.
In the present application, "optionally, in Ar 1 、Ar 2 In which any two adjacent substituents form a ring "means that in Ar 1 Or Ar 2 Any two adjacent substituents may or may not form a ring. For example, when Ar 1 When two adjacent substituents form a ring, the number of carbon atoms of the ring is 5-13, and the ring may be saturated or unsaturated. For example: cyclohexane, cyclopentane, adamantane, benzene ring, naphthalene ring, fluorene ring, and the like, but is not limited thereto.
In the present application, the number of carbon atoms of the substituted or unsubstituted functional group refers to all the numbers of carbon atoms. For example, if L is selected from a substituted arylene group having 12 carbon atoms, then the arylene group and all of the substituents thereon have 12 carbon atoms. For example: ar isThe number of carbon atoms is 7; l is->The number of carbon atoms is 12.
In the present application, "hetero" means that at least 1 hetero atom such as B, N, O, S, P, si or Se is included in one functional group and the remaining atoms are carbon and hydrogen when no specific definition is provided otherwise. Unsubstituted alkyl groups may be "saturated alkyl groups" without any double or triple bonds.
In the present application, "alkyl" may include a straight chain alkyl group or a branched alkyl group. Alkyl groups may have 1 to 10 carbon atoms, and in the present application, a numerical range such as "1 to 10" refers to each integer in the given range; for example, "alkyl of 1 to 10 carbon atoms" refers to an alkyl group that may contain 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. Furthermore, alkyl groups may be substituted or unsubstituted.
Preferably, the alkyl group is selected from alkyl groups having 1 to 5 carbon atoms, and specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and pentyl.
In the present application, cycloalkyl refers to saturated hydrocarbons containing alicyclic structures, including monocyclic and condensed ring structures. Cycloalkyl groups may have 3-10 carbon atoms, a numerical range such as "3 to 10" referring to each integer in the given range; for example, "cycloalkyl of 3 to 10 carbon atoms" refers to cycloalkyl groups that may contain 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, or 10 carbon atoms. Cycloalkyl groups may be substituted or unsubstituted. Examples of cycloalkyl groups are cyclopentylalkyl, cyclohexenyl, adamantyl.
In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups connected by a carbon-carbon bond conjugate. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered as aryl groups of the present application unless otherwise indicated. Among them, the condensed ring aryl group may include, for example, a bicyclic condensed aryl group (e.g., naphthyl group), a tricyclic condensed aryl group (e.g., phenanthryl group, fluorenyl group, anthracenyl group), and the like. The aryl group does not contain hetero atoms such as B, N, O, S, P, se, si and the like. For example, in the present application, biphenyl, terphenyl, etc. are aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, tetrabiphenyl, triphenylene, pyrenyl, benzofluoranthryl,A base, etc.
In the present application, a "substituted or unsubstituted aryl group" may contain from 6 to 30 carbon atoms, in some embodiments the number of carbon atoms in the substituted or unsubstituted aryl group may be from 6 to 25, in some embodiments the number of carbon atoms in the substituted or unsubstituted aryl group may be from 6 to 20, in other embodiments the number of carbon atoms in the substituted or unsubstituted aryl group may be from 6 to 20, and in other embodiments the number of carbon atoms in the substituted or unsubstituted aryl group may be from 6 to 12. For example, in the present application, the number of carbon atoms of the substituted or unsubstituted aryl group may be 6, 12, 13, 14, 15, 18, 20, 24, 25, 28, 29, 30, although other numbers are possible, and are not listed here. In the present application, biphenyl may be understood as phenyl-substituted aryl, and also as unsubstituted aryl.
In the present application, the arylene group refers to a divalent group formed by further losing one hydrogen atom from the aryl group.
In the present application, the substituted aryl group may be one in which one or two or more hydrogen atoms in the aryl group are substituted with a group such as deuterium atom, halogen group, cyano group, aryl group, heteroaryl group, trialkylsilyl group, alkyl group, cycloalkyl group, alkoxy group, or the like. It is understood that the number of carbon atoms of a substituted aryl refers to the total number of carbon atoms of the aryl and substituents on the aryl, e.g., a substituted aryl having 18 carbon atoms refers to the total number of carbon atoms of the aryl and its substituents being 18.
In the present application, specific examples of the aryl group as a substituent include, but are not limited to: phenyl, naphthyl, anthryl, phenanthryl, dimethylfluorenyl, biphenyl, and the like.
In the present application, heteroaryl means a monovalent aromatic ring containing 1, 2, 3, 4 or 5 heteroatoms in the ring or a derivative thereof, and the heteroatoms may be at least one of B, O, N, P, si, se and S. Heteroaryl groups may be monocyclic heteroaryl or polycyclic heteroaryl, in other words, heteroaryl groups may be a single aromatic ring system or multiple aromatic ring systems that are conjugated through carbon-carbon bonds, with either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-arylcarbazolyl (e.g., N-phenylcarbazolyl), N-heteroarylcarbazolyl (e.g., N-pyridylcarbazolyl), N-alkylcarbazolyl (e.g., N-methylcarbazolyl), and the like, without limitation thereto. Wherein thienyl, furyl, phenanthroline and the like are heteroaryl groups of a single aromatic ring system type, and N-phenylcarbazolyl and N-pyridylcarbazolyl are heteroaryl groups of a polycyclic ring system type which are conjugated and connected through carbon-carbon bonds.
In the present application, the heteroarylene group refers to a divalent group formed by further losing one hydrogen atom.
In the present application, a substituted heteroaryl group may be one in which one or more hydrogen atoms in the heteroaryl group are substituted with a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, an alkoxy group, or the like. It is understood that the number of carbon atoms of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and substituents on the heteroaryl.
In the present application, specific examples of heteroaryl groups as substituents include, but are not limited to: pyridyl, carbazolyl, dibenzofuranyl, dibenzothienyl.
In the present application, the halogen group may include fluorine, iodine, bromine, chlorine, and the like.
In the present application, specific examples of the trialkylsilyl group having 3 to 12 carbon atoms include, but are not limited to, trimethylsilyl group, triethylsilyl group and the like.
In the present application, specific examples of the haloalkyl group having 1 to 10 carbon atoms include, but are not limited to, trifluoromethyl.
In the present application, the non-positional connection key means a single bond extending from the ring systemIt means that one end of the bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the remainder of the compound molecule.
For example, as shown in formula (f), the naphthyl group represented by formula (f) is attached to the other positions of the molecule via two non-positional linkages extending through the bicyclic ring, which means includes any of the possible linkages shown in formulas (f-1) -formula (f-10).
As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by the formula (X') is linked to the other position of the molecule through an unoositioned linkage extending from the middle of one benzene ring, and the meaning represented by this linkage includes any possible linkage as shown in the formula (X '-1) -formula (X' -4).
The meaning of the non-positional connection or the non-positional substitution is the same as here, and will not be described in detail later.
In some embodiments of the application, the phosphorescent host material is selected from compounds represented by the following chemical formula:
in some embodiments of the application, n 1 、n 2 、n 3 All 0.
In some embodiments of the application, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
Alternatively, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.
Optionally, the substituent in the L is selected from deuterium, halogen group, cyano, alkyl with 1-5 carbon atoms and phenyl.
Specifically, specific examples of the substituents in L include, but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl.
In other embodiments of the application, L is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenyl.
Alternatively, L is selected from a single bond, phenylene.
In some embodiments of the application, L is selected from the group consisting of a single bond or:
in some embodiments of the application, L 1 、L 2 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
Optionally, the L 1 、L 2 The substituents in (a) are independently selected from deuterium, halogen group, cyano, alkyl with 1-5 carbon atoms and phenyl.
Specifically, the L 1 、L 2 Specific examples of substituents in (a) include, but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl.
In other embodiments of the application, L 1 、L 2 Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted anthryl group.
In some embodiments of the application, L 1 、L 2 Each independently selected from a single bond, a substituted or unsubstituted group G selected from the group consisting of:
wherein ,represents a chemical bond; the substituted group G contains one or more substituents selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl; and when the substituted group G contains a plurality of substituents, the substituents may be the same or different.
Alternatively, L 1 、L 2 Each independently selected from the group consisting of a single bond or:
in some embodiments of the application, ar 1 、Ar 2 Each independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms.
Optionally, the Ar 1 、Ar 2 The substituents in (2) are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1-5 carbon atoms, cycloalkyl group having 5-10 carbon atoms, and aryl group having 6-12 carbon atoms.
Optionally in Ar 1 、Ar 2 Any two adjacent substituents form a saturated or unsaturated ring with 5-13 carbon atoms. Optionally in Ar 1 、Ar 2 Any two adjacent substituents may form cyclohexaneCyclopentane processBenzene ring, naphthalene ring or fluorene ring->
In other embodiments of the application, ar 1 、Ar 2 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, and substituted or unsubstituted triphenylenyl.
Optionally, the Ar 1 、Ar 2 The substituents of (2) are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexenyl, adamantyl, phenyl.
Optionally in Ar 1 、Ar 2 Any two adjacent substituents form a fluorene ring.
In other embodiments of the application, ar 1 、Ar 2 Each independently selected from the group consisting of substituted or unsubstituted groups V selected from the group consisting of:
wherein ,represents a chemical bond; the substituted group V contains one or more substituents selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexenyl, adamantyl, phenyl; and when the substituted group V contains a plurality of substituents, the substituents may be the same or different.
Optionally, the Ar 1 、Ar 2 Each independently selected from the group consisting of:
in some embodiments of the application, a+b is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Optionally, the phosphorescent host material is selected from the group consisting of:
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The present application provides a composition for an organic phosphorescent device light-emitting layer, comprising the phosphorescent host material described above (hereinafter referred to as "first compound for an organic phosphorescent device light-emitting layer") and a second compound for an organic phosphorescent device light-emitting layer, wherein the second compound for an organic phosphorescent device light-emitting layer comprises a phosphorescent host material represented by formula 2:
wherein ,R4 、R 5 、R 6 、R 7 Each independently selected from hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 12 to 25 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, and a cycloalkyl group having 3 to 10 carbon atoms;
n 4 represents a substituent R 4 Number n of (n) 4 Selected from 1, 2, 3 or 4, when n 4 When the number is greater than 1, any two R 4 The same or different;
n 5 represents a substituent R 5 Number n of (n) 5 Selected from 1, 2 or 3, when n 5 When the number is greater than 1, any two R 5 The same or different;
n 6 represents a substituent R 6 Number n of (n) 6 Selected from 1, 2 or 3, when n 6 When the number is greater than 1Any two R 6 The same or different;
n 7 represents a substituent R 7 Number n of (n) 7 Selected from 1, 2, 3 or 4, when n 7 When the number is greater than 1, any two R 7 The same or different;
L 3 、L 4 the same or different and are respectively and independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms and substituted or unsubstituted heteroarylene with 3-30 carbon atoms;
Ar 3 and Ar4 The same or different and are respectively and independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
each R is 4 、R 5 、R 6 、R 7 Wherein the substituent is phenyl;
L 3 、L 4 、Ar 3 and Ar4 The substituents in (2) are the same or different and are each independently selected from deuterium, halogen group, cyano group, heteroaryl group with 3-20 carbon atoms, aryl group with 6-20 carbon atoms, trialkylsilyl group with 3-12 carbon atoms, alkyl group with 1-10 carbon atoms, halogenated alkyl group with 1-10 carbon atoms, cycloalkyl group with 3-10 carbon atoms, heterocycloalkyl group with 2-10 carbon atoms and alkoxy group with 1-10 carbon atoms;
optionally in Ar 3 and Ar4 Any two adjacent substituents form a ring.
In some embodiments of the application, the second compound is selected from the group consisting of compounds represented by the following formulas:
in some embodiments of the application, each R in the second compound 4 、R 5 、R 6 、R 7 Independently selected from hydrogen, deuterium, halogen group, cyano group, substituted or unsubstituted aryl group with 6-18 carbon atoms, substituted or unsubstituted aryl group with 12-20 carbon atoms Heteroaryl, alkyl having 1 to 5 carbon atoms, haloalkyl having 1 to 5 carbon atoms, and cycloalkyl having 3 to 6 carbon atoms.
Alternatively, each R 4 、R 5 、R 6 、R 7 Each independently selected from hydrogen, deuterium, fluorine, methyl, ethyl, n-propyl, isopropyl, t-butyl, substituted or unsubstituted phenyl, naphthyl, substituted or unsubstituted biphenyl, phenanthryl, terphenyl, substituted or unsubstituted carbazolyl.
Further alternatively, R 4 、R 5 、R 6 、R 7 Each independently selected from hydrogen or phenyl.
In some embodiments of the application, each R in the second compound 4 、R 5 、R 6 、R 7 Each independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, or:
in some embodiments of the application, in the second compound, the L 3 and L4 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.
Optionally, the L 3 and L4 The substituents in (a) are independently selected from deuterium, halogen group, cyano, alkyl with 1-5 carbon atoms and phenyl.
Specifically, the L 3 and L4 Specific examples of substituents in (a) include, but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl.
In other embodiments of the present application, in the second compound, the L 3 and L4 Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or substituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstitutedDibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolylene.
In some embodiments of the application, in the second compound, the L 3 and L4 Each independently selected from a single bond, a substituted or unsubstituted group P, wherein the unsubstituted group P is selected from the group consisting of:
wherein ,represents a chemical bond; the substituted group P has one or more substituents thereon, each of which is independently selected from deuterium, cyano, fluoro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl; when the number of substituents of P is greater than 1, the substituents may be the same or different.
Alternatively, L 3 and L4 Each independently selected from the group consisting of a single bond or:
in some embodiments of the application, in the second compound, the Ar 3 and Ar4 Each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms.
Optionally, the Ar 3 and Ar4 The substituents in (2) are independently selected from deuterium, halogen group, alkyl group with 1-5 carbon atoms, and aryl group with 6-12 carbon atoms.
Optionally Ar 3 and Ar4 Any two adjacent substituents of the formula (I) form a saturated or unsaturated ring with 5-13 carbon atoms. Optionally in Ar 3 、Ar 4 Any two adjacent substituents are connected with each other to form cyclopentaneCyclohexane->Benzene ring, naphthalene ring or fluorene ring->
Specifically, the Ar 3 and Ar4 Specific examples of substituents in (a) include, but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl.
In other embodiments of the present application, in the second compound, the Ar 3 and Ar4 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, and substituted or unsubstituted triphenylenyl;
Optionally, the Ar 3 and Ar4 The substituents of (a) are each independently selected from deuterium, fluorine, cyano, halogen radicals, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl.
Optionally Ar 3 and Ar4 Any two adjacent substituents of (a) form a fluorene ring.
In some embodiments of the application, in the second compound, the Ar 3 and Ar4 Each independently selected from the group consisting of substituted or unsubstituted groups W selected from the group consisting of:
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wherein ,represents a chemical bond; the substituted group W has one or more substituents thereon, each of which is independently selected from deuterium, cyano, fluoro, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl, naphthyl, biphenyl; when the number of substituents of W is greater than 1, each substituent is the same or different.
Optionally, in the second compound, the Ar 3 and Ar4 Each independently selected from the group consisting of:
optionally, the second compound is selected from the group consisting of:
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optionally, the composition is a mixture of the first compound and the second compound. For example, the mixture may be formed by mechanically stirring and mixing the first and second compounds uniformly.
The relative amounts of the two types of compounds in the composition are not particularly limited in the present application, and may be selected according to the specific application of the organic electroluminescent device. Typically, the first compound may be present in an amount of 1% to 99% by mass and the second compound may be present in an amount of 1% to 99% by mass, based on the total weight of the composition. For example, the mass ratio of the first compound to the second compound in the composition may be 1:99, 20:80, 30:70, 40:60, 45:65, 50:50, 55:45, 60:40, 70:30, 80:20, 99:1, etc.
In some embodiments of the present application, the composition consists of a first compound and a second compound, wherein the first compound is present in an amount of 20% to 80% by mass and the second compound is present in an amount of 20% to 80% by mass, based on the total weight of the composition.
In some preferred embodiments, the composition comprises, based on the total weight of the composition, 30% -60% by mass of the first compound and 40% -70% by mass of the second compound, and in this case, the composition is applied to an organic electroluminescent device, so that the device has both higher luminous efficiency and longer service life, and is particularly suitable for being used as an electronic display device. Preferably, the mass percentage of the first compound is 40% -60% and the mass percentage of the second compound is 40% -60% based on the total weight of the composition. More preferably, the mass percentage of the first compound is 40% -50%, and the mass percentage of the second compound is 50% -60%.
The application also provides application of the composition as an organic electroluminescent layer main body material of an organic electroluminescent device.
The present application provides an organic electroluminescent device comprising an anode and a cathode disposed opposite each other, and at least one functional layer interposed between the anode and the cathode, the functional layer comprising the phosphorescent host material of the present application or a composition for a light emitting layer of the organic phosphorescent device.
In one embodiment of the present application, the functional layer comprises an organic light-emitting layer comprising the phosphorescent host material of the present application.
In one embodiment of the present application, the functional layer comprises an organic light emitting layer comprising the composition for an organic phosphorescent device light emitting layer of the present application.
In one embodiment of the present application, the organic electroluminescent device is a phosphorescent device.
In one embodiment of the present application, the organic electroluminescent device is a green organic electroluminescent device.
In one embodiment of the present application, as shown in fig. 1, the organic electroluminescent device of the present application includes an anode 100, a cathode 200, and at least one functional layer 300 interposed between the anode layer and the cathode layer, the functional layer 300 including a hole injection layer 310, a hole transport layer 321, a hole auxiliary layer 322, an organic light emitting layer 330, an electron transport layer 350, and an electron injection layer 360.
Optionally, a hole blocking layer 340 may be disposed between the organic light emitting layer 330 and the electron transport layer 350. The organic light emitting layer 330 may contain the organic compound according to the first aspect of the present application.
Alternatively, the anode 100 comprises an anode material, which preferably has a large work function (work function) that facilitates hole injection into the functional layerWork function) material. Specific examples of the anode material include metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metal and oxide such as ZnO, al or SnO 2 Sb; or conductive polymers such as poly (3-methylthiophene) and poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but not limited thereto. It is preferable to include a transparent electrode containing Indium Tin Oxide (ITO) as an anode.
Alternatively, the hole transport layer 321 may include one or more hole transport materials, and the hole transport materials may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not particularly limited in the present application. For example, in some embodiments of the present application, hole transport layer 321 consists of HT-01.
Alternatively, the hole auxiliary layer 322 may include one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not particularly limited in the present application. For example, in some embodiments of the present application, hole assist layer 322 is comprised of HT-02.
Alternatively, the organic light emitting layer 330 may be composed of a single light emitting material, and may include a host material and a guest material. Alternatively, the organic light emitting layer 330 is composed of a host material and a guest material, and holes and electrons injected into the organic light emitting layer 330 may be recombined at the organic light emitting layer 330 to form excitons, which transfer energy to the host material, which transfers energy to the guest material, thereby enabling the guest material to emit light.
The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which are not particularly limited in the present application.
In some embodiments of the present application, a green organic electroluminescent device, the organic light emitting layer 330 comprises Phosphorescent host material, GH-P and guest material Ir (ppy) as described herein 3 。
The electron transport layer 350 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which are not particularly limited in the present application. For example, in some embodiments of the present application, electron transport layer 350 may be composed of ET-01 and LiQ.
Optionally, a hole blocking layer 340 is disposed between the organic light emitting layer 330 and the electron transport layer 350. The hole blocking layer may include one or more hole blocking materials, which are not particularly limited in the present application.
Alternatively, the cathode 200 includes a cathode material that is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multi-layer material such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 /Ca, but is not limited thereto. A metal electrode containing silver and magnesium is preferably included as a cathode.
Optionally, a hole injection layer 310 may also be provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 may be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, and other materials, which are not particularly limited in the present application. In some embodiments of the present application, the hole injection layer 310 may be composed of CuPC.
Optionally, an electron injection layer 360 may also be provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include an inorganic material such as an alkali metal sulfide, an alkali metal halide, or may include a complex of an alkali metal and an organic substance. In some embodiments of the present application, the electron injection layer 360 may include ytterbium (Yb).
The application also provides an electronic device comprising the organic electroluminescent device.
For example, as shown in fig. 2, the electronic device provided by the present application is a first electronic device 400, where the first electronic device 400 includes any one of the organic electroluminescent devices described in the above embodiments of the organic electroluminescent device. The electronic device may be a display device, a lighting device, an optical communication device, or other type of electronic device, which may include, but is not limited to, a computer screen, a cell phone screen, a television, an electronic paper, an emergency light, an optical module, etc. Since the first electronic device 400 has the above-mentioned organic electroluminescent device, the present application has the same beneficial effects and is not described herein.
The present application will be described in detail with reference to examples, but the following description is intended to explain the present application and is not intended to limit the scope of the application in any way.
Synthetic examples
Synthesis of intermediate a 1-1:
phenylboronic acid (10 g;82.03 mmol), 2-bromo-5-chloro-1-iodobenzene (31.24 g;98.44 mmol), tetrakis triphenylphosphine palladium (0.95 g;0.82 mmol), potassium carbonate (24.94 g;180.48 mmol), tetrabutylammonium bromide (2.65 g;3.20 mmol), toluene (240 mL), ethanol (60 mL) and deionized water (60 mL) were added to a round-bottomed flask, and the mixture was stirred and warmed to 75-80℃under nitrogen protection for 16 hours; the reaction mixture was cooled to room temperature, washed with water, and the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; purification of the crude product by column chromatography on silica gel using dichloromethane/n-heptane as eluent afforded intermediate a1-1 (14.05 g, 64%) as a pale yellow solid
Referring to the procedure for intermediate a1-1, using reactant A in Table 1 below in place of phenylboronic acid and reactant B in place of 2-bromo-5-chloro-1-iodobenzene, the intermediate compounds shown in Table 1 below were synthesized:
TABLE 1
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Synthesis of intermediate a 1-2:
intermediate a1-1 (14 g;52.32 mmol), 4-fluorobenzeneboronic acid (7.3 g;52.32 mmol), tetrakis triphenylphosphine palladium (0.61 g;0.52 mmol), potassium carbonate (15.9 g;115.10 mmol), tetrabutylammonium bromide (1.68 g;5.23 mmol), toluene (120 mL), ethanol (30 mL) and deionized water (30 mL) were added to a round bottom flask and stirred under nitrogen protection to raise the temperature to 75-80℃for 16 hours; the reaction mixture was cooled to room temperature, washed with water, and the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; purification of the crude product by column chromatography on silica gel using methylene chloride/n-heptane as eluent afforded intermediate a1-2 (10.95 g; 74%) as a pale yellow solid
Referring to the synthesis of intermediate a1-2, using reactant C in Table 1 below in place of 4-fluorobenzeneboronic acid and reactant D in place of a1-1, the intermediate compounds shown in Table 2 below were synthesized:
TABLE 2
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Synthesis of intermediate a 1-3:
indolo [2,3-A ] carbazole (9.07 g;35.37 mmol), a1-2 (10.00 g;35.37 mmol), tris (dibenzylideneacetone) dipalladium (0.32 g;0.35 mmol), x-phos (0.34 g;0.71 mmol), sodium tert-butoxide (5.10 g;53.06 mmol) and xylene (100 mL) were added to a round-bottomed flask and reacted under nitrogen at 135-140℃for 16 hours; cooling to room temperature, washing the reaction solution with water, separating the reaction solution, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification of the crude product by silica gel column chromatography using methylene chloride/n-heptane as eluent afforded compound intermediate a1-3 (15.34 g; 86%)
Referring to the synthesis of intermediates a1-3, using reactant E in Table 3 below in place of a1-2, the intermediate compounds shown in Table 3 below were synthesized:
TABLE 3 Table 3
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Synthesis of Compound A-1:
intermediate a1-3 (15 g;29.84 mmol), intermediate i1 (7.99 g;29.84 mmol) and N, N-Dimethylformamide (DMF) (150 mL) were added to a round bottom flask, the temperature of the system was reduced to-5℃under nitrogen, and then sodium hydride (1.07 g,44.77 mmol) was added to continue the reaction at room temperature for 12h; washing the reaction solution with water, separating the reaction solution, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification of the crude product by silica gel column chromatography using dichloromethane/n-heptane as eluent followed by recrystallization purification using a toluene/n-heptane solvent system yielded compound A1 (14.32 g, 65%) as mass spectrum M/z=734.3 (m+h) +
Referring to the synthesis of compound A1, using reactant F in table 4 below instead of intermediates A1-3, and reactant F instead of intermediate i1, the intermediate compounds shown in table 4 below were synthesized:
TABLE 4 Table 4
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Mass spectrum data for some compounds are shown in table 5 below:
TABLE 5
| Compound A1 | m/z＝743.3(M+H) + | Compound A4 | m/z＝810.3(M+H) + |
| Compound A7 | m/z＝810.3(M+H) + | Compound A12 | m/z＝828.3(M+H) + |
| Compound A18 | m/z＝904.3(M+H) + | Compound A28 | m/z＝972.2(M+H) + |
| Compound B2 | m/z＝810.3(M+H) + | Compound B6 | m/z＝784.3(M+H) + |
| Compound B8 | m/z＝904.3(M+H) + | Compound B11 | m/z＝752.3(M+H) + |
| Compound B14 | m/z＝852.3(M+H) + | Compound B19 | m/z＝882.3(M+H) + |
| Compound C2 | m/z＝810.3(M+H) + | Compound C4 | m/z＝810.3(M+H) + |
| Compound C9 | m/z＝878.3(M+H) + | Compound C15 | m/z＝878.3(M+H) + |
| Compound D4 | m/z＝784.3(M+H) + | Compound D13 | m/z＝904.3(M+H) + |
| Compound E6 | m/z＝784.3(M+H) + | Compound F6 | m/z＝878.3(M+H) + |
| Compound B7 | m/z＝828.3(M+H) + | Compound A33 | m/z＝828.3(M+H) + |
| Compound A36 | m/z＝886.3(M+H) + | Compound A37 | m/z＝770.3(M+H) + |
| Compound A38 | m/z＝784.3(M+H) + | Compound B29 | m/z＝780.3(M+H) + |
| Compound C25 | m/z＝744.3(M+H) + | Compound C26 | m/z＝846.4(M+H) + |
The nuclear magnetic data of a part of the compounds are shown in Table 6 below
TABLE 6
Synthesis of Compound 324 from preparation 29
(1) Synthesis of intermediate SM-1
4-tert-butylbromobenzene (10 g;46.9 mmol), p-chlorobenzeneboronic acid (7.32 g;46.8 mmol), tetrakis triphenylphosphine palladium (2.7 g;2.3 mmol), potassium carbonate (9.7 g;70.3 mmol), tetrabutylammonium bromide (0.65 g;2.3 mmol), toluene (80 mL), water (20 mL), ethanol (40 mL) were added to the round-bottomed flask and reacted under nitrogen at 110℃for 6 hours with stirring; cooling to room temperature, washing the reaction solution with water, separating the reaction solution, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification of the crude product by silica gel column chromatography using dichloromethane/n-heptane as eluent gave SM-1 (8.6 g, 75% yield).
Referring to the synthesis of SM-1, the intermediate SM-X shown in table 7 below was synthesized using starting material M in table 7 below instead of 4-tert-butylbromobenzene, where X is 2,3,4.
TABLE 7
(2) Synthesis of Compound 324
9- (1, 1 '-Biphenyl) -4-yl-3, 3' -dicarbazole (9.9 g;20.4 mmol), SM1 (5.0 g;20.4 mmol), tris (dibenzylideneacetone) dipalladium (0.18 g;0.2 mmol), 2-dicyclohexylphosphine-2 '6' -dimethoxy-biphenyl (0.17 g;0.4 mmol), sodium t-butoxide (2.9 g;30.6 mmol), xylene (100 mL) were added to a round bottom flask and reacted under nitrogen at 135℃for 16 hours with stirring; cooling to room temperature, washing the reaction solution with water, separating the reaction solution, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using methylene chloride/n-heptane as eluent to give 324 (11.3 g, yield 80%).
Referring to the synthesis method of compound 324, the compounds shown in table 8 below were synthesized using raw material N instead of SM-1 and raw material O instead of 9- (1, 1 '-biphenyl) -4-yl-3, 3' -dicarbazole.
TABLE 8
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Mass spectrum data of the above compounds are shown in the following table 9
TABLE 9
| Compound 324 | m/z＝693.3[M+H] + | Compound 330 | m/z＝655.3[M+H] + |
| Compound 326 | m/z＝586.2[M+H] + | Compound 338 | m/z＝727.3[M+H] + |
| Compound 359 | m/z＝713.3[M+H] + | Compound 382 | m/z＝713.3[M+H] + |
| Compound 340 | m/z＝637.3[M+H] + | Compound 361 | m/z＝731.3[M+H] + |
| Compound 350 | m/z＝726.3[M+H] + | Compound 342 | m/z＝726.3[M+H] + |
| Compound 348 | m/z＝667.2[M+H] + | Compound 378 | m/z＝651.3[M+H] + |
| Compound 365 | m/z＝651.3[M+H] + | Compound 374 | m/z＝713.3[M+H] + |
Preparation and performance evaluation of organic electroluminescent devices
Example 1
Green organic electroluminescent device
An anode is formed of Indium Tin Oxide (ITO) on a substrate with a reflective layer formed thereon, and has a thickness ofCutting into dimensions of 40mm x 0.7mm, preparing an experimental substrate with a cathode, an anode and an insulating layer pattern by adopting a photoetching procedure, and cleaning the surface of the ITO substrate by adopting an organic solvent to remove impurities on the surface of the ITO substrate; or by ultraviolet ozone and O 2 :N 2 Plasma surface treatment to increase the work function of the anode.
Vacuum evaporating CuPC on anode of substrate by PVD method to form a film with thicknessIs deposited on the hole injection layer>HT-01 of (A) forms a hole transport layer.
Vapor deposition on hole transport layerHT-02 of (A) forms a hole assist layer.
On the hole-assist layer, compositions GH-1-1 and Ir (ppy) 3 100%: co-evaporation was performed at a rate of 10% to form a film having a thickness ofAn organic light emitting layer (green organic light emitting layer).
Evaporating ET-01 and LiQ in a ratio of 1:1 to formA thick electron transport layer formed by vapor deposition of Yb on the electron transport layer to a thickness +. >Magnesium and silver at 1:9 vapor deposition ratio is co-evaporated on the electron injection layer to form a thickness of +.>Is provided.
In addition, the thickness of the vapor deposited on the cathode isAn organic capping layer (CPL) is formed, thereby realizing the preparation of an organic light emitting device.
Examples 2 to 28:
in forming the organic light emitting layer, an organic electroluminescent device was fabricated by the same method as in example 1, substituting the composition GH-1-1 in example 1 with the GH-X-Y type host material composition shown in Table 11.
Comparative examples 1-3:
an organic electroluminescent device was prepared in the same manner as in device example 1, except that GH-X-Y was used in forming the organic light-emitting layer.
In the above examples and comparative examples, the host material compositions GH-X-Y used were obtained by mixing the first compound in preparation examples 1 to 28 and the second compound in preparation examples 29 to 42, respectively, and the specific compositions are shown in Table 10, wherein the mass ratio refers to the ratio of the mass percentages of the compounds shown in the front and the compounds shown in the rear in the tables. Taking the composition GH-1-1 as an example, it can be seen in Table 11 that GH-1-1 is prepared from compound A1 and compound 326 according to 50:50 mass ratio; as can be seen from Table 10, by taking the host material GH-D1-1 as an example, GH-D1-1 is prepared by mixing a compound I with a compound 326 in a mass ratio of 40:60.
The material structures used in device examples 1-28 and comparative examples 1-3 are shown in Table 10 below:
table 10
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For the organic electroluminescent device prepared as above, the temperature was 20mA/cm 2 The device performance was analyzed under the conditions, and the results are shown in table 11 below.
TABLE 11
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As can be seen from the data shown in table 11 above, the organic electroluminescent devices prepared in examples 1 to 30 have significantly reduced driving voltage, high luminous efficiency and long service life compared to comparative example 1.
Compared with comparative examples 1-3, the organic electroluminescent devices prepared in examples 1-30 of the present application have a T95 lifetime improved by at least 11.9% and a current efficiency improved by at least 20.9%. Compared with the compounds shown in comparative examples 1-3, the phosphorescent host material provided by the application has obviously improved device performance. The reason for this is probably that the fluorine substituent introduced in the present application effectively improves the electron injection performance of the light emitting layer compared with the compound ii, thereby improving the exciton recombination efficiency. Compared with the compound III, the phosphorescence host material of the application introduces fluorine substituent, but the substituent is positioned on the central phenyl of the 1, 3-diphenyl phenyl, and compared with the phosphorescence host material of the application, the phosphorescence host material of the application has poorer electron injection performance under the condition that the substituent is positioned at the outermost periphery of the molecule, thereby not significantly improving the electronic characteristics.
Therefore, when the phosphorescence host material is used for preparing a green organic electroluminescent device, the luminous efficiency of the organic electroluminescent device can be effectively improved, the voltage can be reduced, and the service life of the organic electroluminescent device can be prolonged.
Other embodiments of the application will be apparent to those skilled in the art from consideration of the specification and practice of the application disclosed herein. This application is intended to cover any variations, uses, or adaptations of the application following, in general, the principles of the application and including such departures from the present disclosure as come within known or customary practice within the art to which the application pertains. It is intended that the specification and examples be considered as exemplary only, with a true scope and spirit of the application being indicated by the following claims.
Claims (9)
1. A phosphorescence host material has a structure shown in formula 1:
wherein each R 1 、R 2 Or R is 3 Each independently selected from deuterium, halogen group, cyano, aryl group of 6-12 carbon atoms, heteroaryl group of 5-12 carbon atoms, alkyl group of 1-5 carbon atoms, haloalkyl group of 1-5 carbon atoms, cycloalkyl group of 3-10 carbon atoms;
n 1 represents a substituent R 1 Number n of (n) 1 Selected from 0;
n 2 represents a substituent R 2 Number n of (n) 2 Selected from 0;
n 3 represents a substituent R 3 Number n of (n) 3 Selected from 0;
l is selected from a single bond, a substituted or unsubstituted phenylene group;
L 1 、L 2 each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group;
the substituents in the L are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl;
the L is 1 、L 2 Each substituent of (a) is independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, phenyl;
Ar 1 、Ar 2 each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, and substituted or unsubstituted terphenyl;
the Ar is as follows 1 、Ar 2 Wherein each substituent is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl or phenyl;
a. b is independently selected from 0, 1, 2, 3, 4 or 5, and a+b is not less than 1.
2. The phosphorescent host material according to claim 1, ar 1 、Ar 2 Each independently selected from the group consisting of substituted or unsubstituted groups V selected from the group consisting of:
wherein ,represents a chemical bond; the substituted group V contains one or more substituents each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; and when the substituted group V contains a plurality of substituents, the substituents may be the same or different.
3. The phosphorescent host material according to claim 1, selected from the group consisting of:
4. a composition for a light emitting layer of an organic phosphorescent device comprising a first compound and a second compound;
the first compound comprising the phosphorescent host material according to any one of claims 1 to 3, and the second compound being selected from compounds represented by formulae 2 to 3:
wherein each R 4 、R 5 、R 6 、R 7 Each independently selected from hydrogen, deuterium, fluorine, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl;
n 4 represents a substituent R 4 Number n of (n) 4 Selected from 1,2,3 or 4, when n 4 When the number is greater than 1, any two R 4 The same or different;
n 5 represents a substituent R 5 Number n of (n) 5 Selected from 1,2 or 3, when n 5 When the number is greater than 1, any two R 5 The same or different;
n 6 represents a substituent R 6 Number n of (n) 6 Selected from 1,2 or 3, when n 6 When the number is greater than 1, any two R 6 The same or different;
n 7 represents a substituent R 7 Number n of (n) 7 Selected from 1,2,3 or 4, when n 7 When the number is greater than 1, any two R 7 The same or different;
L 3 and L4 Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted carbazolylene group;
The L is 3 and L4 The substituents in (a) are each independently selected from deuterium, fluorine, cyano, methylEthyl, n-propyl, isopropyl, t-butyl, phenyl;
Ar 3 and Ar4 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted carbazolyl;
the Ar is as follows 3 and Ar4 The substituents in (a) are each independently selected from deuterium, fluorine, cyano, halogen radicals, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl.
5. The composition for an organic phosphorescent device light-emitting layer according to claim 4, wherein the second compound is selected from the group consisting of:
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6. an organic electroluminescent device comprises an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode;
the functional layer contains the phosphorescent host material according to any one of claims 1 to 3 or the composition for an organic phosphorescent device light-emitting layer according to claim 4 or 5.
7. The organic electroluminescent device of claim 6, wherein the functional layer comprises an organic light-emitting layer.
8. The organic electroluminescent device of claim 6, wherein the organic electroluminescent device is a green organic electroluminescent device.
9. An electronic device comprising an organic electroluminescent device as claimed in any one of claims 6 to 8.
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| TW202124387A (en) * | 2019-11-21 | 2021-07-01 | 南韓商Ｌｔ素材股份有限公司 | Heterocyclic compound, organic light emitting device and composition for forming organic material layer |
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