CN115433193A

CN115433193A - Compound and application thereof in organic photoelectric device

Info

Publication number: CN115433193A
Application number: CN202211031672.XA
Authority: CN
Inventors: 王鹏; 王湘成; 何睦
Original assignee: Shanghai Yaoyi Electronic Technology Co ltd
Current assignee: Shanghai Yaoyi Electronic Technology Co ltd
Priority date: 2022-08-26
Filing date: 2022-08-26
Publication date: 2022-12-06

Abstract

The invention discloses a compound and application thereof in an organic photoelectric device, wherein the chemical structure of the compound is shown as the formula (I), wherein X is ₁ ～X ₃ Selected from single bonds, -NR ₁₀ -, O or S, R ₁ ～R ₁₀ The same or different, independently selected from hydrogen, deuterium, substituted or unsubstituted straight chain or branched chain C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl or ring bonding with adjacent atoms. The compound has higher triplet state energy level, better carrier mobility, good thermal stability and good film forming stability, can be matched with adjacent energy levels, and can reduce driving voltage and improve the luminous efficiency of a device when being used as a main material for red and green phosphorescent OLED devices.

Description

Compound and application thereof in organic photoelectric device

Technical Field

The invention belongs to the field of organic photoelectric materials, and particularly relates to a compound and application thereof in an organic photoelectric device.

Background

Organic Light Emission Diodes (OLED) devices are devices having a sandwich-like structure, including positive and negative electrode films and Organic functional material layers sandwiched between the electrode films, and have been widely applied to display panels of products such as novel lighting fixtures, smart phones and tablet computers, and will also be expanded to the application field of large-size display products such as televisions, and are a novel display technology with fast development and high technical requirements.

With the development of multimedia information technology, the requirements for the performance of flat panel display devices are increasing. The main display technologies at present are plasma display devices, field emission display devices, and organic electroluminescent display devices (OLEDs). The OLED has a series of advantages of self luminescence, low-voltage direct current driving, full curing, wide viewing angle, rich colors and the like, and compared with a liquid crystal display device, the OLED does not need a backlight source, has a wider viewing angle and low power consumption, has the response speed 1000 times that of the liquid crystal display device, and has a wider application prospect.

Since the first time OLEDs were reported, many scholars have been devoted to studying how to improve device efficiency and stability. Forrest and Thompson research groups find that the transition metal complex can be applied to Ph OLEDs (phosphorescent OLEDs), the phosphorescent material has strong spin-orbit coupling effect, and singlet excitons and triplet excitons can be simultaneously utilized, so that the quantum efficiency in the phosphorescent electroluminescent device theoretically reaches 100%. However, the phosphorescent material has a long excited state life, and when the concentration of triplet excitons is high, triplet-20944extinct and triplet-polaron-20944extinct are easily formed, so that the phosphorescent material is often taken as an object to be added into a host material to reduce a self-concentration quenching process, and the selection of a proper host material in a phosphorescent organic electroluminescent device is very important.

With the wide commercial application of OLED display and illumination, the requirements of the client terminal on the photoelectricity and service life of the OLED screen body are also continuously improved, and in order to meet the requirements, in addition to the refinement on the OLED panel manufacturing process, the development of OLED materials capable of meeting higher device indexes is also important. The following properties are required as host materials for phosphorescent organic electroluminescent devices: (1) has a higher triplet energy level; (2) The carrier mobility is better and can be matched with the energy level of the adjacent layer; (3) has high thermal stability and film-forming stability. Therefore, a stable and efficient main body material is developed and used for the OLED display device, so that the driving voltage is reduced, the light emitting efficiency of the device is improved, the service life of the device is prolonged, and the OLED display device has important practical application value.

Disclosure of Invention

The invention mainly aims to provide a stable and efficient compound which can be used for red and green phosphorescent OLED devices, has higher triplet state energy level and better carrier mobility, can be matched with adjacent energy levels, has good thermal stability and film forming stability, can reduce driving voltage when being used for the red and green phosphorescent OLED devices, and improves the luminous efficiency of the devices.

The invention provides a compound, which has a chemical structure shown as a formula (I):

in the formula (I), X ₁ ～X ₃ Selected from single bonds, -NR ₁₀ -, O or S;

R ₁ ～R ₁₀ the two groups are the same or different, and are respectively and independently selected from hydrogen, deuterium, substituted or unsubstituted straight-chain or branched-chain C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl or are bonded with adjacent atoms to form a ring.

The present invention also provides a host material comprising at least one of said compounds as a first host compound; or further comprising at least one second host compound represented by general formula (ii):

in the formula (II), ar ₁ 、Ar ₂ And Ar ₃ The same or different, each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl or bonded with adjacent atoms to form a ring.

The present invention also provides an organic layer comprising at least one of said compounds or at least one of said host materials.

The invention also provides an organic photoelectric device which comprises a first electrode, a second electrode and the organic layer, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer or an electron transport layer.

The invention also provides a display or lighting device comprising the organic photoelectric device.

Compared with the prior art, the invention has the following beneficial effects: according to the compound provided by the invention, because the central ring is a large power supply system ring, the HOMO energy level of the whole molecule is concentrated on the central ring, so that the HOMO energy level and the LUMO energy level are well separated, and the electron transport capacity of the whole molecule is improved. In addition, the HOMO energy level of the molecule is more concentrated, and after a strong electron-withdrawing group is introduced, the triplet state energy level of the molecule is in a higher level, so that the molecule is suitable for red light and green light host materials. Furthermore, the molecule as a whole has a cyclic structure, which improves the thermal stability of the molecule. The compound provided by the invention is applied to an organic photoelectric device, so that the device has higher efficiency, and meanwhile, the molecules have high stability, and the luminous efficiency and the service life of the device can be further improved.

Detailed Description

Embodiments of the specifically disclosed compounds and their use in organic opto-electronic devices are described in detail below. Other advantages and effects of the present invention will be readily apparent to those skilled in the art from the disclosure herein. The invention is capable of other and different embodiments and of being practiced or of being carried out in various ways, and its several details are capable of modification in various respects, all without departing from the spirit and scope of the present invention.

Before the present embodiments are further described, it is to be understood that the scope of the invention is not limited to the particular embodiments described below; it is also to be understood that the terminology used in the examples is for the purpose of describing particular embodiments, and is not intended to limit the scope of the present invention; in the description and claims of the present application, the singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise.

When numerical ranges are given in the examples, it is understood that both endpoints of each of the numerical ranges and any value therebetween can be selected unless the invention otherwise indicated. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In addition to the specific methods, devices, and materials used in the examples, any methods, devices, and materials similar or equivalent to those used in the examples may be used in the practice of the invention, in addition to those described herein, in keeping with the knowledge of one skilled in the art and the present disclosure.

Examples of the substituent in the present invention are described below, but the substituent is not limited thereto:

[ substituted or unsubstituted ] means substituted with one or more substituents selected from: deuterium, a halogen group, a nitrile group, nitro, hydroxyl, carbonyl, an ester group, an imide group, amino, a phosphine oxide group, alkoxy, aryloxy, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, silyl, boryl, alkyl, cycloalkyl, alkenyl, aryl, aralkyl, aralkenyl, alkylaryl, alkylamino, aralkylamino, heteroarylamino, arylamino, arylphosphino and heteroaryl, acenaphthenyl or unsubstituted; or substituted with a substituent linking two or more of the substituents exemplified above, or unsubstituted, e.g., "a substituent linking two or more substituents" may include a biphenyl group, i.e., the biphenyl group may be an aryl group, or a substituent linking two phenyl groups.

[ alkyl ] may be a linear or branched alkyl group, and the number of carbon atoms is not particularly limited. In some embodiments, alkyl includes, but is not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl.

The above description of alkyl groups also applies to alkyl groups in aralkyl, aralkylamino, alkylaryl, and alkylamino groups.

[ heteroalkyl ] may be a linear or branched alkyl group containing a heteroatom, and the number of carbon atoms is not particularly limited. In some embodiments, heteroalkyl includes, but is not limited to, alkoxy, alkylthio, alkylsulfonyl, and the like; alkoxy includes, but is not limited to, methoxy, ethoxy, n-propoxy, isopropoxy (isoproxy), isopropoxy (i-propyloxy), n-butoxy, isobutoxy, t-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, and the like; alkylthio includes, but is not limited to, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, tert-butylthio, sec-butylthio, n-pentylthio, neopentylthio, isopentylthio, n-hexylthio, 3-dimethylbutylthio, 2-ethylbutylthio, n-octylthio, n-nonylthio, n-decylthio, benzylthio, and the like.

[ cycloalkyl ] may be a cyclic cycloalkyl group, and the number of carbon atoms is not particularly limited. In some embodiments, cycloalkyl includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like.

[ heterocycloalkyl ] may be a cycloalkyl group containing a heteroatom, and the number of carbon atoms is not particularly limited. In some embodiments, heterocycloalkyl includes, but is not limited to

And the like.

[ aryl ] is not particularly limited, and may be a monocyclic aryl group or a polycyclic aryl group. In some embodiments, monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, and the like; polycyclic aryl groups include, but are not limited to, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, fluorenyl, and the like, and the fluorenyl group can be substituted, such as 9,9 '-dimethylfluorenyl, 9' -dibenzofluorenyl, and the like. In addition, two of the substituents may be bonded to each other to form a spiro ring structure, for example, 9,9' -spirobifluorenyl group and the like.

The above description of aryl groups applies to arylene groups, except that arylene groups are divalent.

The above description of aryl groups applies to aryl groups in aryloxy, arylthio, arylsulfonyl, arylphosphino, aralkyl, aralkylamino, aralkenyl, alkylaryl, arylamino, and arylheteroarylamino groups.

[ heteroaryl ] comprises one or more of N, O, P, S, si and Se as a heteroatom. Heteroaryl groups include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, pyrazinyl, oxazinyl, thiazinyl, dioxanyl, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthenyl, phenanthridinyl, naphthyridinyl, triazainonyl, indolyl, indolinyl, indolizinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, furanyl, thienyl, thiazolyl, and the like pyrazinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, indenocarbazolyl, phenazinyl, imidazopyridinyl, phenazinyl, phenanthridinyl, phenanthrolinyl, phenothiazinyl, imidazopyridinyl, imidazophenanthridinyl, benzimidazoloquinazolinyl, benzimidazolophenanthridinyl, spiro [ fluorene-9, 9' -xanthene ], benzidinaphthyl, dinaphthofuranyl, naphthobenzofuranyl, dinaphthothiophenothienyl, naphthobenzothienyl, triphenylphosphine oxide, triphenylborane, and the like.

The above description of heteroaryl groups applies to heteroaryl groups in heteroarylamino and arylheteroarylamino groups.

The above description of heteroaryl is applicable to heteroarylenes, except that heteroarylenes are divalent.

Specifically, the chemical structure represented by formula (i) may be unsubstituted or substituted with one or more substituents selected from, for example, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amine group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamine group, an arylheteroarylamino group, an arylphosphino group, and a heteroaryl group.

The compound takes a multi-heterocyclic structure as a matrix, the matrix structure has good thermal stability, proper HOMO, LUMO energy levels and Eg, higher triplet state energy level, better carrier mobility, higher thermal stability and film forming stability, is a novel OLED material, and can effectively improve the efficiency and the service life of a device when being applied to a main body material of an OLED device.

In some embodiments, in formula (I), R ₁₀ At least one selected from the group consisting of:

wherein R is ₁₁ ～R ₁₅ The two groups are the same or different, and are respectively and independently selected from hydrogen, deuterium, substituted or unsubstituted straight-chain or branched-chain C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl or are bonded with adjacent atoms to form a ring.

In some embodiments, the compound of formula (i) is selected from one or more of the following chemical structures:

the present invention also provides a host material comprising at least one compound represented by formula (i) as a first host compound, or further comprising at least one second host compound represented by general formula (ii):

In some embodiments, the second host compound of formula (ii) is selected from one or more of the following chemical structures:

in some embodiments, the host material comprises at least one compound selected from the group consisting of chemical structures represented by H-1 through H-107 as a first host compound and at least one second host compound selected from the group consisting of chemical structures represented by E-1 through E-100.

In one aspect, the present invention provides an organic layer comprising the compound of the present invention as described above.

In one aspect the present invention provides the use of a compound according to the invention as hereinbefore described and/or an organic layer as hereinbefore described in an organic opto-electronic device.

The organic photoelectric device provided by the invention comprises a first electrode, a second electrode and one or more organic layers arranged between the first electrode and the second electrode, and is of a bottom or top light-emitting device structure, wherein the organic layers can be of a single-layer structure or a multi-layer series structure laminated with two or more organic layers, for example, the organic layers comprise at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer or an electron transport layer, and can be prepared by using common methods and materials for preparing organic photoelectric devices, and the compound provided by the invention is used as the organic layers of the organic photoelectric devices.

In the organic photoelectric device provided by the invention, the first electrode is used as an anode layer, and the anode material can be a material with a large work function, so that holes can be smoothly injected into the organic layer; for example, a metal oxide, a combination of a metal and an oxide, a conductive polymer, or the like may be used, and the metal oxide may be, for example, indium Tin Oxide (ITO), zinc oxide, indium Zinc Oxide (IZO), or the like.

In the organic photoelectric device provided by the invention, the second electrode is used as a cathode layer, the cathode material can be a material with a small work function, for example, so that electrons can be smoothly injected into the organic layer, the cathode material can be metal or a material with a multilayer structure, for example, the metal can be magnesium, silver, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, tin, lead or an alloy thereof, and the cathode material is preferably magnesium and silver.

In the organic opto-electronic device provided by the present invention, the material of the hole injection layer, preferably the material having the Highest Occupied Molecular Orbital (HOMO) between the work function of the anode material and the HOMO of the surrounding organic layer, is the material that advantageously receives holes from the anode at low voltage.

In the organic photoelectric device provided by the present invention, the material of the hole transport layer is a material having high mobility to holes, and is suitable for receiving holes from the anode or the hole injection layer and transporting the holes to the light emitting layer, and includes, but is not limited to, organic materials of arylamine, conductive polymers, block copolymers having both conjugated and non-conjugated portions, and the like.

In the organic photoelectric device provided by the invention, the compound provided by the invention can be applied to a light-emitting layer of the device.

In the organic photoelectric device provided by the present invention, the material of the electron transport layer is a material having high mobility to electrons and suitable as a material that advantageously receives electrons from the cathode and transports the electrons to the light emitting layer.

In the organic photoelectric device provided by the invention, the material of the covering layer generally has high refractive index, which is beneficial to improving the light efficiency of the organic light-emitting device, especially the external light-emitting efficiency.

The organic photoelectric device provided by the invention is an organic photovoltaic device, an organic light-emitting device, an organic solar cell, electronic paper, an organic photoreceptor, an organic thin film transistor and the like.

In one aspect, the present invention provides a display or lighting device comprising the organic optoelectronic device of the present invention.

The technical solution of the present invention is further explained by specific examples below.

Synthesis examples:

the synthesis of the compound represented by the above formula (I) can be carried out by a known method. For example, a cross-coupling reaction using a transition metal such as nickel or palladium, and another synthesis method is a C-C or C-N coupling reaction using a transition metal such as magnesium or zinc. The reaction is limited to mild reaction conditions, superior selectivity of various functional groups and the like, and Suzuki and Buchwald reactions are preferred. The compounds of the present invention are illustrated by, but not limited to, the following examples. The initial raw materials and solvents of the invention and some common products such as OLED intermediates are purchased from domestic OLED intermediate manufacturers; various palladium catalysts, ligands, etc. are available from sigma-Aldrich. ¹ H-NMR data were measured using a JEOL (400 MHz) nuclear magnetic resonance apparatus, and HPLC data were measured using a Shimadzu LC-20AD high performance liquid chromatograph.

The materials used in the examples were:

example 1

Synthesis of Compound 1

1) Synthesis of intermediate 1-1

16.7g (100 mmol) of the compound 1-A, 1-B24.7g (100 mmol) of the compound, 800mg (12.5 mmol) of activated copper powder and 10.3g (75 mmol) of potassium carbonate were charged into a reaction vessel under an argon and nitrogen atmosphere, and 500ml of xylene was added to conduct a reflux reaction overnight. After completion of cooling to room temperature, filtration under reduced pressure was carried out, and the crude product was stirred with 500ml of water for 3 times, and the obtained crude product was purified by silica gel column chromatography (ethyl acetate/petroleum ether = 1. LC MS: M/Z333.07 (M +). ¹ H-NMR(400MHz,DMSO-d6)δ7.32–7.40(m,4H),7.59–7.67(m,2H),7.82(t,1H),8.16–8.24(m,2H),8.71(d,2H).

2) Synthesis of Compound 1-2

To a reaction vessel were added, under an argon atmosphere, compound 1-1.33 g (100 mmol), triphenylphosphine 65.5g (250 mmol) and potassium carbonate 27.6g (200 mmol), and THF 800mL was added. After the mixture was heated to reflux for 24 hours, it was cooled to room temperature, and the mixture was diluted with 500mL of ethyl acetate and 500mL of water was used to wash the organic layer three times, and the organic layer was concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel (ethyl acetate/petroleum ether =1 50) to obtain the product compound 1-218.9g, with hplc purity 99.5% and yield 70%. LC MS: M/Z269.10 (M +). ¹ H-NMR(400MHz,DMSO-d ₆ )δ6.75(t,2H),6.95(d,2H),7.12(dd,2H),7.22(t,1H),8.10(m,2H).

3) Synthesis of Compound 1

Under an argon atmosphere, to a reaction vessel were added 1 to 2.9 g (100 mmol) of the compound 1 to C57.0 g (200 mmol), 23.4g (240 mmol) of sodium tert-butoxide, 575mg (1 mmol) of palladium bis-dibenzylideneacetone, and tri-tert-butylphosphine tetrakisFluoroborate (580 mg, 2 mmol%) and 1000mL of xylene (xylene) were stirred at 140 ℃ for 15 hours. The reaction mixture was cooled to room temperature, 1000ml of water was added, filtered, the filter cake was washed with a large amount of water, dried in vacuo, and the crude product was purified by silica gel column chromatography (eluent: ethyl acetate/petroleum ether =1 = 100) to give 54.2g of compound 1, hplc purity 99.9%, yield 80%. LC MS: M/Z677.23 (M +). ¹ H-NMR(400MHz,DMSO-d6)δ6.75(m,2H),6.95(d,2H),7.12(m,2H),7.22(t,1H),7.37–7.54(m,4H),7.60–7.70(m,4H),7.72–7.84(m,8H),8.10(m,2H),8.27(m,2H).

Example 2

Synthesis of Compound 31

The procedure was as in example 1 except that the starting materials were changed to 31-A and 31-C. LC MS M/Z809.24 (M +). The total synthesis yield is as follows: 35 percent; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d6)δ6.74–6.79(m,2H),6.82(m,2H),6.88–6.97(m,3H),7.29(m,2H),7.37–7.46(m,2H),7.60–7.76(m,8H),7.76–7.84(m,4H),8.01(d,2H),8.08–8.14(m,2H),8.23–8.31(m,2H),8.48–8.54(m,2H).

Example 3

Synthesis of Compound 50

The procedure was repeated in the same manner as in example 1 except that the starting material was changed to 50-C. LC MS M/Z809.33 (M +). The total synthesis yield is as follows: 36 percent; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d ₆ )δ1.69(s,12H),6.75(m,2H),6.95(d,2H),7.12(m,2H),7.22(t,1H),7.27–7.43(m,6H),7.43(d,10H),7.97(m,2H),8.10(m,2H).

Example 4

Synthesis of Compound 73

The procedure of example 2 was repeated, except that the starting material was changed to 73-C. LC MS M/Z789.19 (M +). The total synthesis yield is as follows: 31 percent; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d ₆ )δ6.74–6.79(m,2H),6.82(m,2H),6.88–6.97(m,3H),7.29(m,2H),7.32–7.46(m,6H),7.60–7.70(m,6H),7.76–7.84(m,4H),7.97–8.07(m,2H).

Example 5

Synthesis of Compound 93

The procedure of example 2 was repeated, except that the starting materials were changed to 93-A and 93-C. LC MS M/Z923.31 (M +). The total synthesis yield is as follows: 35 percent; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d ₆ )δ6.31(m,2H),6.74–6.83(m,4H),6.83(m,2H),6.92(m,1H),7.12–7.23(m,4H),7.37–7.46(m,2H),7.44–7.51(m,4H),7.52–7.70(m,10H),7.76–7.84(m,4H),8.17–8.26(m,2H),8.54–8.64(m,2H).

Example 6

Synthesis of Compound 113

The procedure was repeated in the same manner as in example 1 except that the starting material was changed to 113-C. LC MS M/Z653.23 (M +). The total synthesis yield is as follows: 31 percent; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d ₆ )δ6.75(m,2H),6.95(d,2H),7.12(m,2H),7.18–7.25(m,3H),7.28(m,2H),7.33–7.40(m,4H),7.44–7.52(m,4H),7.55–7.65(m,4H),8.10(m,2H),8.53–8.59(m,2H).

Example 7

Synthesis of Compound 136

The procedure of example 2 was repeated, except that the starting material was changed to 136-C. LC MS M/Z739.23 (M +). The total synthesis yield is as follows: 31 percent; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d ₆ )δ6.74–6.79(m,2H),6.82(m,2H),6.88–6.97(m,3H),7.29(m,2H),7.39–7.47(m,3H),7.43–7.51(m,4H),7.47–7.54(m,1H),7.51–7.59(m,4H),7.71–7.79(m,4H),8.03–8.11(m,4H).

Example 8

Synthesis of Compound 150

The procedure was as in example 2 except that the starting material was changed to 150-C. LC MS M/Z763.23 (M +). The total synthesis yield is as follows: 32 percent; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d ₆ )δ6.74–6.79(m,2H),6.82(m,2H),6.88–6.97(m,3H),7.29(m,2H),7.44–7.55(m,12H),8.30–8.40(m,8H).

Example 9

Synthesis of Compound 183

The procedure was as in example 1 except that the starting material was changed to 183-C. LC MS M/Z503.14 (M +). The total synthesis yield is as follows: 33 percent; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d ₆ )δ6.75(m,2H),6.95(d,2H),7.12(m,2H),7.22(t,1H),7.48–7.63(m,8H),8.10(m,2H).

Example 10

Synthesis of Compound 205

The procedure of example 2 was repeated, except that the starting materials were changed to 93-A, 205-B and 150-C. LC MS M/Z914.32 (M +). The total synthesis yield is as follows: 31 percent; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d ₆ )δ6.31(m,2H),6.75(s,2H),6.79(t,2H),6.83(m,2H),7.00(m,2H),7.04–7.12(m,4H),7.20–7.29(m,4H),7.44–7.55(m,12H),8.30–8.40(m,8H).

Example 11

Synthesis of Compound H-1

The procedure was as in example 1 except that the starting material was changed to H-1-C. LC MS M/Z421.16 (M +). The total synthesis yield is as follows: 36 percent; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d ₆ )δ6.75(m,2H),6.92–7.04(m,4H),7.04–7.15(m,6H),7.18–7.29(m,5H),8.10(m,2H).

Example 12

Synthesis of Compound H-15

The procedure of example 1 was repeated, except that the starting material was changed to H-15-C. LC MS M/Z621.22 (M +). The total synthesis yield is as follows: 31 percent; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d ₆ )δ6.75(m,2H),6.92–7.01(m,4H),7.12(m,2H),7.22(t,1H),7.35–7.46(m,4H),7.50–7.59(m,4H),7.96–8.06(m,4H),8.10(m,2H),8.20(t,2H),8.30(t,2H).

Example 13

Synthesis of Compound H-29

The procedure of example 1 was repeated, except that the starting material was changed to H-29-C. LC MS M/Z621.22 (M +). The total synthesis yield is as follows: 33%; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d ₆ )δ6.75(m,2H),6.95(d,2H),7.12(m,2H),7.22(t,1H),7.56–7.78(m,8H),7.84(m,2H),7.87–7.94(m,2H),8.00–8.06(m,2H),8.10(m,2H),8.27(d,2H),8.74–8.80(m,2H).

Example 14

Synthesis of Compound H-37

The procedure of example 2 was repeated, except that the starting material was changed to H-37-C. LC MS M/Z617.17 (M +). The total synthesis yield is as follows: 35 percent; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d ₆ )δ6.31(m,2H),6.74–6.87(m,6H),6.92(m,1H),6.97(m,2H),7.31(m,2H),7.45(m,2H),7.51–7.59(m,4H),7.95–8.02(m,2H),8.19–8.24(m,2H).

Example 15

Synthesis of Compound H-50

The procedure was as in example 1 except that the starting material was changed to H-50-C. LC MS M/Z653.28 (M +). The total synthesis yield is as follows: 33 percent; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d ₆ )δ1.69(s,12H),6.75(m,2H),6.95(d,2H),7.12(m,2H),7.22(t,1H),7.27(m,2H),7.35(m,2H),7.42–7.56(m,6H),7.83–7.91(m,4H),8.10(m,2H).

Example 16

Synthesis of Compound H-58

The procedure was as in example 2 except that the starting material was replaced with H-58-C. LC MS M/Z767.27 (M +). The total synthesis yield is as follows: 34 percent; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d ₆ )δ6.31(m,2H),6.74–6.87(m,6H),6.92(m,1H),7.19(m,2H),7.31–7.40(m,6H),7.44–7.51(m,4H),7.52–7.67(m,10H),8.20(m,2H).

Example 17

Synthesis of Compound H-72

The procedure was as in example 2 except that the starting material was replaced with H-72-C. LC MS M/Z769.24 (M +). The total synthesis yield is as follows: 33%; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d ₆ )δ6.31(m,2H),6.74–6.87(m,6H),6.92(m,1H),7.32–7.51(m,10H),7.56–7.62(m,2H),7.75–7.83(m,4H),7.98–8.06(m,2H),8.13(d,2H),8.20(d,2H).

Example 18

Synthesis of Compound H-85

The procedure of example 1 was repeated, except that the starting material was changed to H-85-C. LC MS M/Z967.28 (M +). The total synthesis yield is as follows: 31 percent; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d6)δ6.71–6.82(m,4H),6.92–7.00(m,4H),6.96–7.04(m,2H),7.04–7.14(m,12H),7.15(d,1H),7.15–7.25(m,7H),7.21–7.29(m,3H),7.34–7.48(m,6H),8.10(m,2H).

Example 19

Synthesis of Compound H-89

The procedure was as in example 2 except that the starting material was changed to H-89-C. LC MS M/Z757.26 (M +). The total synthesis yield is as follows: 36 percent; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d ₆ )δ6.74–6.79(m,2H),6.82(m,2H),6.88–6.97(m,3H),7.29(m,2H),7.34–7.43(m,4H),7.43–7.53(m,8H),7.69–7.77(m,8H),7.87(d,4H),8.36(t,2H).

Example 20

Synthesis of Compound H-102

The procedure was as in example 10 except that the starting material was replaced with H-89-C. LC MS M/Z757.26 (M +). The total synthesis yield is as follows: 31 percent; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d6)δ6.74–6.79(m,2H),6.82(m,2H),6.88–6.97(m,3H),7.29(m,2H),7.34–7.43(m,4H),7.43–7.53(m,8H),7.69–7.77(m,8H),7.87(d,4H),8.36(t,2H).

Example 21

Synthesis of Compound E-5

1) Synthesis of intermediate E-5-1

31.5g (100 mmol) of E-5-A, 17.2g (100 mmol) of E-5-B, 1.16g (1.0 mmol) of tetrakis (triphenylphosphine) palladium, 200ml (300 mmol) of 1.5M aqueous sodium carbonate solution and 800ml of ethylene glycol dimethyl ether (DME) were charged into a reactor under an argon atmosphere, and the mixture was stirred at 80 ℃ overnight. After cooling to room temperature, 500ml of water was added to precipitate a solid, which was filtered off, and the obtained solid was washed with ethanol to obtain 27.9g of compound E-5-1, yield 77%, and HPLC purity 99.5%. LC MS M/Z361.02 (M +); ¹ H-NMR(400MHz,DMSO-d6)δ7.44–7.55(m,3H),7.56–7.68(m,2H),7.96–8.05(m,1H),8.08(d,1H),8.11–8.20(m,1H),8.30–8.40(m,2H),8.49(dd,1H),9.09(t,1H).

2) Synthesis of Compound E-5

Under an argon atmosphere, E-5-1.36 g (100 mmol), E-5-C30.0 g (100 mmol), tetrakis (triphenylphosphine) palladium 1.16g (1.0 mmol), 1.5M aqueous sodium carbonate solution 200ml (300 mmol) and ethylene glycol dimethyl ether 800ml (DME) were charged into a reactor, and the mixture was heated and stirred overnight at 80 ℃. After cooling to room temperature, 500ml of water was added, a solid precipitated and filtered, and the obtained solid was washed with ethanol to give 44.6g of compound E-5, yield 83%, HPLC purity 99.9%. LC MS M/Z537.20 (M +); ¹ H-NMR(400MHz,DMSO-d6)δ7.37–7.45(m,2H),7.45–7.57(m,5H),7.57–7.68(m,2H),7.72–7.78(m,1H),7.78–7.85(m,1H),7.96–8.04(m,1H),8.04–8.11(m,2H),8.11–8.20(m,1H),8.24–8.31(m,2H),8.31–8.40(m,2H),8.45–8.53(m,1H),8.69–8.76(m,1H),8.76–8.82(m,1H),9.09(t,1H).

example 22

Synthesis of Compound E-15

The procedure was as in example 21 except that the starting material was changed to E-15-B. LC MS M/Z544.15 (M +). The total synthesis yield is as follows: 61%; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d6)δ7.31–7.59(m,9H),7.72–7.78(m,1H),7.78–7.85(m,1H),7.85–7.91(m,1H),8.02–8.11(m,2H),8.24–8.35(m,2H),8.31–8.40(m,2H),8.69–8.76(m,1H),8.76–8.82(m,1H).

Example 23

Compound E-26

The procedure of example 21 was repeated, except that the starting materials were changed to E-26-B and E-26-C. LC MS M/Z550.22 (M +). The total synthesis yield is as follows: 48 percent; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d ₆ )δ7.19(m,1H),7.32–7.43(m,2H),7.44–7.53(m,6H),7.53–7.66(m,7H),7.69–7.75(m,2H),7.75–7.82(m,2H),7.88–7.96(m,2H),8.01(m,1H),8.17–8.23(m,1H),8.30–8.40(m,2H).

Example 24

Synthesis of Compound E-34

The procedure was as in example 21 except that the starting materials were changed to E-34-A, E-34-B and E-34-C. LC MS M/Z639.19 (M +). The total synthesis yield is as follows: 40 percent; purity by HPLC：99.9％。 ¹ H-NMR(400MHz,DMSO-d ₆ )δ7.31(m,2H),7.49(m,6H),7.60–7.79(m,8H),7.91(d,2H),7.98(m,2H),8.17(m,1H),8.33(m,1H),8.95(d,1H),9.04–9.11(m,1H),9.60(m,1H).

Example 25

Synthesis of Compound E-47

The procedure of example 21 was repeated, except that the starting materials were changed to E-47-B and E-47-C. LC MS M/Z667.27 (M +). The total synthesis yield is as follows: 45 percent; HPLC purity: 99.9 percent. ¹ HNMR(400MHz,DMSO-d6)δ1.69(s,6H),7.28(m,1H),7.35(m,3H),7.42–7.57(m,8H),7.57–7.65(m,1H),7.61–7.71(m,2H),7.78–7.84(m,1H),7.85–7.91(m,1H),7.93–8.01(m,1H),8.08(dd,2H),8.30–8.40(m,2H),8.45–8.53(m,2H),8.56(dd,1H),9.09(dd,2H).

Example 26

Synthesis of Compound E-59

The procedure was repeated in the same manner as in example 21 except that the starting materials were changed to E-59-A, E-59-B and E-59-C. LC MS M/Z627.27 (M +). The total synthesis yield is as follows: 45 percent; HPLC purity: 99.9 percent. ¹ HNMR(400MHz,DMSO-d6)δ1.69(s,6H),7.31–7.77(m,19H),7.85–7.97(m,3H),7.95–8.02(m,2H),8.10–8.17(m,1H),8.46–8.54(m,1H),9.07(t,1H).

Example 27

Synthesis of Compound E-65

The procedure was repeated in the same manner as in example 21 except that the starting materials were changed to E-34-A and E-15-B. LC MS M/Z601.11 (M +). The total synthesis yield is as follows: 45 percent; HPLC purity: 99.9 percent. ¹ H-NMR(400MHz,DMSO-d ₆ )δ7.35(m,2H),7.38–7.49(m,4H),7.49–7.59(m,2H),7.72–7.78(m,1H),7.78–7.85(m,1H),7.88(m,2H),8.02–8.11(m,3H),8.24–8.32(m,2H),8.69–8.76(m,1H),8.76–8.82(m,1H).

Example 28

Synthesis of Compound E-77

31.8g (100 mmol) of E-34-A, 63.6g (300 mmol) of E-34-B, 1.16g (1.0 mmol) of tetrakis (triphenylphosphine) palladium, 200ml (300 mmol) of a 1.5M aqueous solution of sodium carbonate and 800ml (DME) were charged into a reactor under an argon atmosphere, and the mixture was stirred overnight at 80 ℃. After cooling to room temperature, 500ml of water was added, a solid precipitated and was filtered, and the obtained solid was washed with ethanol to obtain 47.5g of compound E-77, yield 82%, and HPLC purity 99.9%. LC MS M/Z579.16 (M +); ¹ H-NMR(400MHz,DMSO-d ₆ )δ7.31(m,3H),7.45(m,3H),7.54(m,3H),7.70(m,3H),7.76(m,3H),7.91(d,3H),7.95–8.02(m,3H).

example 29

Synthesis of Compound E-87

The procedure was as in example 21 except that the starting materials were changed to E-59-A, E-34-C and E-87-C. LC MS M/Z601.22 (M +). The total synthesis yield is as follows: 46 percent; HPLC purity: 99.9 percent. ¹ HNMR(400MHz,DMSO-d6)δ7.31(m,1H),7.35–7.62(m,9H),7.63–7.82(m,8H),7.88–7.95(m,3H),7.95–8.05(m,1H),8.01–8.08(m,1H),8.26–8.34(m,1H),8.46–8.54(m,1H),8.70(t,1H),8.95(m,1H).

Example 30

Synthesis of Compound E-96

The procedure was repeated in the same manner as in example 21 except that the starting materials were changed to E-35-A, E-25-B and E-96-C. LC MS M/Z567.19 (M +). The total synthesis yield is as follows: 41 percent; HPLC purity: 99.9 percent. ¹ HNMR(400MHz,DMSO-d6)δ6.78–6.86(m,2H),6.89–6.99(m,3H),7.08(dd,1H),7.34–7.43(m,2H),7.43–7.53(m,4H),7.54–7.61(m,4H),7.64(dd,1H),7.69–7.77(m,4H),7.88–7.96(m,4H).

Device example 1: preparation of single-main-body material organic electroluminescent device

The basic structural model of an organic optoelectronic device is: ITO/HAT-CN (10 nm)/TAPC (40 nm)/TCTA (10 nm)/EML (compound of the invention) RD (Ir complex) = 94.

A method of fabricating an organic opto-electronic device:

(1) A transparent anodic Indium Tin Oxide (ITO) 20 (10. Omega./sq) glass substrate was subjected to ultrasonic cleaning with acetone, ethanol and distilled water in this order, and then treated with ozone plasma for 15 minutes.

(2) After an ITO substrate is arranged on a substrate fixer of vacuum vapor deposition equipment, the system pressure is controlled to be 10 ^-6 Then HAT-CN with a thickness of 10nm, TAPC with a thickness of 40nm and TCTA with a thickness of 10nm were sequentially deposited on the ITO substrate.

(3) And (2) evaporating a light-emitting layer (EML) with the thickness of 40nm on the TCTA, wherein the mass ratio of the compound 1 to RD is 94:6.

(4) An Electron Transport Layer (ETL) material was deposited on the light-emitting layer to a thickness of 30 nm.

(5) LiF with the thickness of 1nm is evaporated on the electron transport layer to be used as an electron injection layer.

(6) Al with the thickness of 80nm is evaporated on the electron injection layer to be used as a cathode, and the device is packaged by a glass packaging cover.

Device examples 2 to 10

An organic electroluminescent device was produced in the same manner as in device example 1, except that in the formation of the light-emitting layer, compounds 31, 50, 73, 93, 113, 136, 150, 183, and 205 were used instead of compound 1.

Comparative device examples 1 to 2

An organic electroluminescent device was fabricated in the same manner as in device example 1, except that in the formation of the light-emitting layer, the compound RH-01 and the compound RH-02 were used instead of the compound 1.

For the organic electroluminescent device prepared above, the working voltage and efficiency were calculated by a computer-controlled Keithley 2400 testing system. The lifetime of the device under dark conditions was obtained using a Polaronix (mccience co.) lifetime measurement system equipped with a power supply and a photodiode as a detection unit. Each set of device examples and device comparative example 1 was produced and tested in the same batch as the device of device comparative example 2, with the results shown in table 1.

TABLE 1

As can be seen from the results in table 1, when used as the light-emitting layer of the light-emitting device, the compounds used in device examples 1 to 10 all had higher luminous efficiencies (up to 23%) and longer lifetimes of 41% or more than those of the devices formed from the compounds used in device comparative examples 1 and 2. Accordingly, the device structures in the above examples and comparative examples were identical except for the light emitting layer, and the current efficiency of the devices comprising the compound of the present invention was significantly improved and the lifetime thereof was also improved with reference to the device performances of RH-01 and RH-02.

Device example 11: preparation of multi-host material organic electroluminescent device

The basic structural model of the device is as follows: ITO/HAT-CN (10 nm)/TAPC (40 nm)/TCTA (10 nm)/EML (host material of the invention: RD (Ir complex) (40 nm) =98

The method for manufacturing the organic photoelectric device comprises the following steps:

(1) Carrying out ultrasonic cleaning on a transparent anode Indium Tin Oxide (ITO) 20 (10 omega/sq) glass substrate by using acetone, ethanol and distilled water in sequence, and then treating for 15 minutes by using ozone plasma;

(2) After an ITO substrate is arranged on a substrate fixer of vacuum vapor deposition equipment, the system pressure is controlled to be 10 ^-6 Sequentially evaporating HAT-CN with the thickness of 10nm, TAPC with the thickness of 40nm and TCTA with the thickness of 10nm on the ITO substrate;

(3) And (3) depositing a light-emitting layer (EML) having a thickness of 40nm (wherein the mass ratio of the host material of the present invention to RD is 98: 3;

(4) Evaporating an Electron Transport Layer (ETL) material with the thickness of 30 nm;

(5) Evaporating LiF with the thickness of 1nm as an electron injection layer;

(6) And finally, evaporating Al with the thickness of 80nm as a cathode, and packaging the device by using a glass packaging cover.

The device test results are shown in table 2.

Device examples 12 to 20

An organic electroluminescent device was fabricated in the same manner as in device example 11, except that in the formation of the light-emitting layer, the compounds H-1 and E-5 were replaced with the compound compositions H-15 and E-15, H-29 and E-26, H-37 and E-34, H-50 and E-47, H-58 and E-59, H-72 and E-65, H-85 and E-77, H-89 and E-87, H-102 and E-96, respectively.

Comparative device examples 3 to 4

An organic electroluminescent device was fabricated in the same manner as in device example 11, except that in the formation of the light-emitting layer, the compounds CBP, ref1 and Ref2 were used instead of the compounds H-1 and E-5, respectively.

For the organic electroluminescent device prepared above, the working voltage and efficiency were calculated by a computer-controlled Keithley 2400 testing system. The device lifetimes in the dark were obtained using a Polaronix (McScience co.) lifetime measurement system equipped with a power supply and a photodiode as the detection unit, and the devices of each set of device examples and device comparative examples 3 and 4 were produced and tested in the same batch, as shown in table 2.

TABLE 2

From the results of table 2, it is understood that when the compounds used in device examples 11 to 20 were used as the light-emitting layer of the light-emitting device, the voltage was decreased, the light-emitting efficiency was improved (up to 41%) and the lifetime was improved by 36% or more, as compared with the devices formed from the compounds used in device comparative examples 3 and 4. Accordingly, the device structures in the above examples and comparative examples are consistent except for the difference in the light emitting layer, and the current efficiency of the device including the compound of the present invention is remarkably improved and the lifetime thereof is also improved with reference to the device performances of Ref1 and Ref 2.

The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered as the technical solutions and the inventive concepts of the present invention within the technical scope of the present invention.

Claims

1. A compound having the chemical structure of formula (I):

in the formula (I), X ₁ ～X ₃ Independently selected from single bonds, -NR ₁₀ -, O or S;

R ₁ ～R ₁₀ the same or different, are independently selected from hydrogen, deuterium, substituted or unsubstituted straight chain or branched C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstitutedUnsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, or a ring bonded to an adjacent atom.

2. A compound according to claim 1, wherein in formula (I), R is ₁₀ At least one selected from the group consisting of:

wherein R is ₁₁ ～R ₁₅ The same or different, independently selected from hydrogen, deuterium, substituted or unsubstituted straight chain or branched chain C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl or ring bonding with adjacent atoms.

3. A compound according to claim 1, wherein in formula (I), X ₁ And X ₂ Are identical and are each selected from the group consisting of-NR ₁₀ -, while X ₃ Selected from a single bond, O or S.

4. The compound of claim 1, wherein the compound of formula (i) is selected from one or more of the following chemical structures:

5. the compound of claim 1, wherein the compound of formula (i) is selected from one or more of the following chemical structures:

6. a host material comprising at least one compound according to any one of claims 1 to 5 as a first host compound; or further comprising at least one second host compound, and the second host compound is represented by general formula (ii):

in the formula (II), ar ₁ 、Ar ₂ And Ar ₃ The same or different, each is independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl or is bonded with adjacent atoms to form a ring.

7. Host material according to claim 6, characterized in that the second host compound of formula (II) is selected from one or more of the following chemical structures:

8. host material according to claim 7, characterized in that the first host compound is selected from one or more of the compounds of claim 5, while the second host compound is selected from one or more of the chemical structures of claim 7.

9. An organic layer comprising one or more of the compounds of any one of claims 1 to 5, or one or more of the host materials of any one of claims 5 to 7.

10. An organic optoelectronic device comprising a first electrode, a second electrode, and the organic layer of claim 9, the organic layer being at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, or an electron transport layer.

11. The organic optoelectronic device according to claim 10, wherein the organic optoelectronic device is at least one of an organic photovoltaic device, an organic light emitting device, an organic solar cell, electronic paper, an organic photoreceptor, and an organic thin film transistor.

12. A display or lighting device comprising the organic optoelectronic device of any one of claims 10 or 11.