CN119059873A - Organic compound, mixture, composition and organic light-emitting device - Google Patents

Abstract

The application discloses an organic compound, a mixture, a composition and an organic light-emitting device, wherein the organic compound has a structure represented by a formula (I): The organic compound provided by the application has high color purity and good thermal stability, and can effectively improve the stability, luminous efficiency and service life of an organic light-emitting device.

Description

Organic compound, mixture, composition and organic light-emitting device

Technical Field

The application relates to the field of display, in particular to an organic compound, a mixture, a composition and an organic light-emitting device.

Background

An Organic Light-Emitting Diode (OLED) generally has an anode, a cathode, and an Organic functional layer therebetween, and converts electric energy into Light energy using an Organic substance of the Organic functional layer, thereby realizing Organic electroluminescence. In order to improve the luminous efficiency and the service life of the organic electroluminescent element, the organic functional layers are often multiple layers, and the organic matters in each layer are different. Specifically, the organic functional layer mainly includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. A voltage is applied between an anode and a cathode of the organic electroluminescent element, the anode injects holes into the organic functional layer, the cathode injects electrons into the organic functional layer, the injected holes meet the electrons to form excitons, and the excitons emit light when transiting to a ground state, thereby realizing the light emission of the organic electroluminescent element. The organic electroluminescent element has the characteristics of self-luminescence, high brightness, high efficiency, low-voltage driving, wide viewing angle, high contrast, high response and the like, so that the organic electroluminescent device has wide application prospect.

In order to improve the luminous efficiency of the organic electroluminescent element, various luminescent material systems based on fluorescence and phosphorescence have been developed. The reliability of the organic electroluminescent element of the blue fluorescent material is higher, but the emission spectrum of most blue fluorescent materials is too wide, the color purity is poor, the high-end display is not facilitated, the synthesis process of the fluorescent materials is complex, the large-scale mass production is not facilitated, and meanwhile, the OLED stability of the blue fluorescent materials still needs to be further improved.

The current blue light organic electroluminescent element light-emitting layer adopts a host-guest doped structure. Most of blue light host materials adopt condensed ring derivatives based on anthracene, most of blue light guest materials adopt aryl vinyl amine compounds, however, the compounds have poor thermal stability and are easy to decompose, so that the service life of devices is poor, and the compounds have poor color purity and are difficult to realize deep blue light emission, so that the problems of realizing full-color displays exist.

Therefore, development of a blue light emitting material with high color purity and good thermal stability is needed to effectively improve the stability, luminous efficiency and life of the organic light emitting device, enhance the color gamut of the display, and improve the display effect.

Disclosure of Invention

The embodiment of the application provides an organic compound, a mixture, a composition and an organic light-emitting device, and the organic compound provided by the application has high color purity and good thermal stability, and can effectively improve the stability, the luminous efficiency and the service life of the organic light-emitting device, thereby improving the color gamut of a display and improving the display effect.

Embodiments of the present application provide an organic compound having a structure represented by formula (I):

Wherein,

N1 is 0, 1 or 2, n2 is 0, 1 or 2, and n1, n2 are not simultaneously 0;

Ar ¹ and Ar ² independently have one of the following structures:

Wherein,

X is selected from CR ₁ or N;

Y is selected from NR ₂、CR₂R₃、SiR₂R₃, O, S, S =o or SO ₂;

R ₁、R₂、R₃ is independently selected from the group consisting of-H, -D, straight chain alkyl having 1 to 20C atoms, straight chain alkoxy having 1 to 20C atoms, straight chain thioalkoxy having 1 to 20C atoms, branched alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, CF ₃, cl, br, F, I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 60 heteroatoms;

when Ar ¹ and Ar ² are independently selected from benzene rings, R ₁ on the benzene rings are not simultaneously H.

In some embodiments, the Ar ¹ and Ar ² independently have one of the following structures:

Wherein, represents the site of attachment.

In some embodiments, the Ar ¹ and Ar ² independently have one of the structures represented by A1 to A7:

In some embodiments, the organic compound is selected from the group consisting of compounds represented by formulas II-1 through II-10:

In some embodiments, the R ₁ is selected from-H, -D, a straight chain alkyl group having 1 to 10C atoms, a branched alkyl group having 3 to 10C atoms, a cyclic alkyl group having 3 to 10C atoms, or phenyl.

In some embodiments, the organic compound is selected from compounds represented by the following structures:

embodiments of the present application also provide a mixture comprising at least one organic compound as described above and at least one organic functional material selected from a hole injecting material, a hole transporting material, an electron injecting material, an electron blocking material, a hole blocking material, a light emitting material, a host material, or an organic dye.

Embodiments of the present application also provide a composition comprising at least one organic compound as described above and at least one organic solvent, or a mixture as described above and at least one of the organic solvents.

Embodiments of the present application also provide an organic light emitting device including:

a first electrode;

A second electrode disposed opposite to the first electrode, and

An organic functional layer between the first electrode and the second electrode;

Wherein the material of the organic functional layer comprises at least one organic compound as described above, or the material of the organic functional layer comprises a mixture as described above.

In some embodiments, the organic functional layer includes at least a light emitting layer including a host material including the organic compound and a guest material including a compound represented by formula (III):

Wherein,

Ar ³、Ar⁴、Ar⁵、Ar⁶、Ar⁷ is independently selected from at least one of a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 60 ring atoms.

In some embodiments, the Ar ³、Ar⁴、Ar⁵、Ar⁶、Ar⁷ independently has one of the following structures:

Wherein:

V is selected from CR ₄ or N;

W is selected from NR ₅、CR₅R₆、SiR₅R₆, O, S, S =o or SO ₂;

R ₄、R₅、R₆ is independently selected from the group consisting of-H, -D, straight chain alkyl having 1 to 20C atoms, straight chain alkoxy having 1 to 20C atoms, straight chain thioalkoxy having 1 to 20C atoms, branched alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, CF ₃, cl, br, F, I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 60 heteroatoms.

In some embodiments, the formula (III) has one of the following structures:

The application provides an organic compound represented by a formula I, which comprises deuterium benzene, anthracene and phenanthrene structures, but when only an anthracene group is connected between deuterium benzene and phenanthrene, the anthracene group can degrade conjugation between molecules, so that the performance of a light-emitting device is degraded, according to the application, new aromatic ring groups Ar ¹ and Ar ² with conjugated structures are introduced between the structures of deuterium benzanthracene and phenanthrene so as to increase the overall conjugation of the organic compound molecules, and simultaneously, the introduced aromatic ring groups increase the molecular weight and improve the thermal stability of the organic compound molecules. In addition, the organic compound of the present application has fluorescence emission with a light emission wavelength at a short wavelength, and its light emission spectrum is represented as having a narrow half-width, so that the substance has fluorescence emission of deep blue, and can be used as a light-emitting material in a light-emitting layer of an organic light-emitting device. Therefore, the organic compound provided by the application has good thermal stability and high color purity, and can effectively improve the stability, luminous efficiency and service life of an organic light-emitting device when being matched with a guest material represented by a formula III (boron nitrogen compound), thereby improving the color gamut of a display and improving the display effect.

Drawings

Fig. 1 is a schematic structural diagram of an organic light emitting device according to an embodiment of the present application.

Detailed Description

It should be understood that the detailed description and specific examples, while indicating and illustrating the application, are not intended to limit the application. In the present application, unless otherwise indicated, terms of orientation such as "upper" and "lower" are used to generally refer to the upper and lower positions of the device in actual use or operation, and in particular to the orientation of the drawing figures. In the present application, "optional" and "optional" refer to the existence or nonexistence of the solution, that is, any one of the two parallel solutions "existence" or "nonexistence" is selected, if multiple "optional" solutions occur in one solution, if no special description exists, and no contradiction or mutual constraint relation exists, each "optional" is independent. In the application, the technical characteristics described in an open mode comprise a closed technical scheme composed of the listed characteristics and also comprise the open technical scheme of the listed characteristics.

In the present application, the composition and the printing ink, or ink, have the same meaning and are interchangeable.

In the present application, aromatic groups and aromatic ring systems have the same meaning and can be interchanged.

In the present application, the heteroaromatic groups, heteroaromatic groups and heteroaromatic ring systems have the same meaning and can be interchanged.

In the present application, "substituted" means that a hydrogen atom in a substituted group is substituted by a substituent. "substituted or unsubstituted" means that the groups defined may or may not be substituted. When the defined groups are substituted, it is understood that they are optionally substituted with a group acceptable in the art, including but not limited to C _1-30 alkyl, a heterocyclic group containing 3 to 20 ring atoms, an aryl group containing 5 to 20 ring atoms, a heteroaryl group containing 5 to 20 ring atoms, a silyl group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a haloformyl group, a formyl group, -NRR ', a cyano group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a trifluoromethyl group, a nitro group or a halogen, and the above groups may be further substituted with a group acceptable in the art, and it is understood that R and R ' in-NRR ' are each independently a group acceptable in the art, including but not limited to H, C _1-6 alkyl, a cycloalkyl group containing 3 to 8 ring atoms, a heterocyclic group containing 3 to 8 ring atoms, an aryl group containing 5 to 20 ring atoms or a heteroaryl group containing 5 to 10 ring atoms, and the C _1-6 alkyl group, a cycloalkyl group containing 3 to 8 ring atoms, a cycloalkyl group containing 3 to 20 ring atoms, a cycloalkyl group containing 5 to 10 ring atoms, a heteroaryl group containing 5 to 10 ring atoms, a further amino group containing 3 to 8 ring atoms, a cycloalkyl group containing 3 to 20 ring atoms, a cycloalkyl group containing 3 to 5 to 8 ring atoms, a halogen atom, a further amino group containing 5 to _1-6, or a further amino group is optionally substituted with a group acceptable in the art.

In the present application, the same substituent may be independently selected from different groups when it appears multiple times. If the general formula contains a plurality of R ¹, R ¹ can be independently selected from different groups. For exampleThe 6R ¹ groups on the benzene ring may be the same or different from each other.

The number of substituents satisfying the substitution rule, e.gN in (2) represents the number of substituents, o may be selected from 0, 1, 2, 3,4,5, 6, 7 or 8,N of (2) may be selected from 0,1, 2, 3, 4, 5 or 6.

In the present application, "substituted or unsubstituted" means that the defined group may or may not be substituted. When the defined groups are substituted, it is understood that they are optionally substituted with a group acceptable in the art, including but not limited to C1-30 alkyl, a heterocyclic group containing 3-20 ring atoms, an aryl group containing 5-20 ring atoms, a heteroaryl group containing 5-20 ring atoms, a silane group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a haloformyl group, a formyl group, -NRR ', a cyano group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a trifluoromethyl group, a nitro group or a halogen, and the above groups may be further substituted with a group acceptable in the art, it being understood that R and R ' in-NRR ' are each independently a group acceptable in the art, including but not limited to H, C-6 alkyl groups, cycloalkyl groups containing 3-8 ring atoms, heterocyclic groups containing 3-8 ring atoms, aryl groups containing 5-20 ring atoms or heteroaryl groups containing 5-10 ring atoms, and the C1-6 alkyl groups, 3-8 cycloalkyl groups containing 3-8 ring atoms, 3-5 ring atoms, aryl groups containing 5-10 ring atoms or heteroaryl groups containing 5-10 ring atoms, the above groups may be further substituted with a group acceptable in the art, such as described above.

In the present application, the "number of ring atoms" means the number of atoms among atoms constituting the ring itself of a structural compound (for example, a monocyclic compound, a condensed ring compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound) in which atoms are bonded to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below, unless otherwise specified. For example, the number of ring atoms of the benzene ring is 6, the number of ring atoms of the naphthalene ring is 10, and the number of ring atoms of the thienyl group is 5.

In the present application, an aromatic ring system or aromatic group refers to a hydrocarbon group containing at least one aromatic ring, and includes monocyclic groups and polycyclic ring systems. Heteroaromatic ring systems or heteroaromatic groups refer to hydrocarbon groups (containing heteroatoms) containing at least one heteroaromatic ring, including monocyclic groups and polycyclic ring systems. The heteroatoms are preferably selected from Si, N, P, O, S and/or Ge, particularly preferably from Si, N, P, O and/or S. These polycyclic rings may have two or more rings in which two carbon atoms are shared by two adjacent rings, i.e., fused rings. Polycyclic, these ring species, at least one of which is aromatic or heteroaromatic. For the purposes of the present application, aromatic or heteroaromatic groups include not only aromatic or heteroaromatic systems, but also systems in which a plurality of aromatic or heteroaromatic groups may also be interrupted by short non-aromatic units (< 10% of non-H atoms, preferably less than 5% of non-H atoms, such as C, N or O atoms). Thus, systems such as9, 9' -spirobifluorene, 9-diaryl fluorene, triarylamine, diaryl ether, and the like are likewise considered aromatic groups for the purposes of this application.

Specifically, examples of the aromatic group are benzene, naphthalene, anthracene, phenanthrene, perylene, naphthacene, pyrene, benzopyrene, triphenylene, naphthacene acenaphthene, fluorene, and derivatives thereof.

Specifically, examples of heteroaromatic groups are furan, benzofuran, thiophene, benzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furopyrrole, furofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, phthalazine, quinoxaline, phenanthridine, primary pyridine, quinazoline, quinazolinone, and derivatives thereof.

In the present application, "alkyl" may denote a linear, branched and/or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-hexyloctyl, 3, 7-dimethyloctyl cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-eicosyl, N-docosanyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc.

In the present application "×" attached to a single bond represents a linking or fusing site.

In the present application, when no attachment site is specified in a group, an optionally attachable site in the group is represented as an attachment site.

In the present application, when no condensed site is specified in the group, it means that an optionally condensed site in the group is used as a condensed site, and preferably two or more sites in the group in the ortho position are condensed sites.

In the present application, a single bond to which a substituent is attached extends through the corresponding ring, meaning that the substituent may be attached to an optional position on the ring, e.gR in (C) is connected with any substitutable site of benzene ring. Such asRepresentation ofCan be combined withOptionally condensed to form a fused ring, preferably adjacent C atoms on the benzene ring.

In the embodiment of the application, the energy level structure of the organic material plays a key role in the triplet energy level ET1, the highest occupied orbital energy level HOMO and the lowest unoccupied orbital energy level LUMO. The determination of these energy levels is described below.

HOMO and LUMO energy levels can be measured by photoelectric effects such as XPS (X-ray photoelectron spectroscopy) and UPS (ultraviolet electron spectroscopy) or by cyclic voltammetry (hereinafter referred to as CV). Recently, quantum chemical methods, such as density functional theory (hereinafter abbreviated as DFT), have also become effective methods for calculating molecular orbital energy levels.

The triplet energy level ET1 of the organic material can be measured by low temperature Time resolved luminescence spectroscopy or obtained by quantum simulation calculations (e.g. by Time-DEPENDENT DFT), such as by commercial software Gaussian09W (Gaussian inc.), specific simulation methods can be seen in WO2011141110 or as described in the examples below.

It should be noted that the absolute value of HOMO, LUMO, ET1 depends on the measurement or calculation method used, and even for the same method, different evaluation methods, e.g. starting and peak points on the CV curve, may give different HOMO/LUMO values. Thus, a reasonable and meaningful comparison should be made with the same measurement method and the same evaluation method. In the description of the embodiments of the present application, the value HOMO, LUMO, ET is based on a simulation of Time-DEPENDENT DFT, but does not affect the application of other measurement or calculation methods.

Embodiments of the present application provide an organic compound having a structure represented by formula (I):

Wherein,

N1 is 0, 1 or 2, n2 is 0, 1 or 2, and n1, n2 are not simultaneously 0;

Ar ¹ and Ar ² are independently at least one selected from a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 14 ring atoms;

When Ar ¹ and Ar ² are independently selected from benzene rings, the substituents on the benzene rings are not simultaneously H.

In some embodiments, the Ar ¹ and Ar ² independently have one of the following structures:

Wherein,

X is selected from CR ₁ or N;

Y is selected from NR ₂、CR₂R₃、SiR₂R₃, O, S, S =o or SO ₂;

R ₁、R₂、R₃ is independently selected from the group consisting of-H, -D, straight chain alkyl having 1 to 20C atoms, straight chain alkoxy having 1 to 20C atoms, straight chain thioalkoxy having 1 to 20C atoms, branched alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, CF ₃, cl, br, F, I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 60 heteroatoms;

When Ar ¹ and Ar ² are independently selected from benzene rings, the substituents R ₁ on the benzene rings are not simultaneously H.

It is understood that in the present application, when X is a binding site, X is C.

Further, the Ar ¹ and Ar ² independently have one of the following structures:

Wherein,

X is selected from CR ₁ or N;

R ₁ is selected from the group consisting of-H, -D, straight chain alkyl having 1 to 20C atoms, straight chain alkoxy having 1 to 20C atoms, straight chain thioalkoxy having 1 to 20C atoms, branched alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, CF ₃, cl, br, F, I, substituted or unsubstituted aromatic group having 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, and at least one of substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms;

when Ar ¹ and Ar ² are independently selected from benzene rings, R ₁ on the benzene rings are not simultaneously H.

In some embodiments, the Ar ¹ and Ar ² independently have one of the following structures:

Wherein, represents the site of attachment;

when Ar ¹ and Ar ² are independently selected from benzene rings, R ₁ on the benzene rings are not simultaneously H.

Further, the Ar ¹ and Ar ² independently have one of the following structures:

Wherein, represents the site of attachment;

when Ar ¹ and Ar ² are independently selected from benzene rings, R ₁ on the benzene rings are not simultaneously H.

When Ar ¹ and Ar ² are selected fromWhen the molecular conjugation of the organic compound is enhanced, the molecular weight of the organic compound is not excessively increased.

In some embodiments, the Ar ¹ and Ar ² independently have one of the structures represented by A1 to A7:

Wherein, represents the site of attachment;

when Ar ¹ and Ar ² are independently selected from benzene rings, R ₁ on the benzene rings are not simultaneously H.

In some embodiments Ar ¹ may be preferably a structure represented by A1

In some embodiments, the Ar ¹ and Ar ² independently have one of the structures represented by B1 to B5:

Wherein, represents the site of attachment;

when Ar ¹ and Ar ² are independently selected from benzene rings, R ₁ on the benzene rings are not simultaneously H.

In some embodiments Ar ² may preferably be a structure represented by B1 or B2

In some embodiments, R ₁ is selected from-H, -D, straight chain alkyl having 1 to 10C atoms, branched alkyl having 3 to 10C atoms, cyclic alkyl having 3 to 10C atoms, or phenyl. When Ar ¹ and Ar ² are independently selected from benzene rings, R ₁ on the benzene rings are not simultaneously H.

Further, R ₁ is selected from the group consisting of-H, -D, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3, 7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, or 2- (2-methyl) butyl.

In some embodiments, R ₂、R₃ is independently selected from-H, -D, a straight chain alkyl group having 1 to 10C atoms, a branched alkyl group having 3 to 10C atoms, a cyclic alkyl group having 3 to 10C atoms, or phenyl.

In some embodiments, n1 may be 0 or 1 or 2, n2 may be 0 or 1 or 2, but n1 and n2 are not both 0 and n1+n2 is 1 or more. For example, n1 is 1, n2 is 0, or n2 is 1, n1 is 0, or both n1 and n2 are 1, but are not limited thereto.

In some embodiments, the organic compound is selected from the group consisting of compounds represented by formulas II-1 through II-10:

in some embodiments, R ₁ in formulas II-1 through II-10 is selected from the group consisting of-H, -D, straight chain alkyl having 1 to 10C atoms, branched alkyl having 3 to 10C atoms, cyclic alkyl having 3 to 10C atoms, or phenyl.

Further, R ₁ in formulas II-1 to II-10 is selected from-H, -D or methyl.

In some embodiments, the organic compound is selected from compounds represented by the following structures:

in some embodiments, the organic compound may be used as an organic functional material in an organic functional layer of an organic light emitting device, in particular an OLED device. The organic functional material includes a Hole Injection Material (HIM), a Hole Transport Material (HTM), an Electron Transport Material (ETM), an Electron Injection Material (EIM), an Electron Blocking Material (EBM), a Hole Blocking Material (HBM), a light emitting body (Emitter), a Host material (Host), an organic dye, and the like.

In some embodiments, the organic compound of the present application may be used in a light emitting layer as a light emitting material, for example, the organic compound may be used in a light emitting layer as a light emitting layer host material.

Embodiments of the present application also provide a mixture comprising at least one organic compound as described above and at least one organic functional material selected from a hole injecting material, a hole transporting material, an electron injecting material, an electron blocking material, a hole blocking material, a light emitting material, a host material, or an organic dye.

In some embodiments, the organic functional material is selected from a host material. For example, the organic functional material may be selected from blue host materials.

Embodiments of the present application also provide a composition comprising at least one organic compound as described above and at least one organic solvent, or a mixture as described above and at least one of the organic solvents.

Wherein the organic solvent comprises at least one of aromatic or heteroaromatic, ester, aromatic ketone or aromatic ether, aliphatic ketone or aliphatic ether, alicyclic or olefin compound, boric acid ester or phosphate ester compound.

In some embodiments, the organic solvent is selected from aromatic or heteroaromatic based solvents. Aromatic or heteroaromatic based solvents include, but are not limited to, p-diisopropylbenzene, pentylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1, 4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluenes, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3, 4-tetramethylbenzene, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2, 4-trichlorobenzene, 4-difluorodiphenyl methane, 1, 2-dimethoxy-4- (1-propenyl) benzene, diphenyl methane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α -dichlorodiphenyl methane, 4- (3-phenylpropyl) pyridine, benzyl benzoate, 1, 4-bis (3, 4-dimethylquinoline), ethyl-benzoate, 2-dimethylfuran, and the like.

In some embodiments, the organic solvent is selected from aromatic ketone-based solvents. Solvents based on aromatic ketones include, but are not limited to, 1-tetralone, 2- (phenylepoxy) tetralone, 6- (methoxy) tetralone, acetophenone, propiophenone, benzophenone, and derivatives thereof, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropophenone, 3-methylpropophenone, 2-methylpropophenone, and the like.

In some embodiments, the organic solvent is selected from aromatic ether-based solvents. Aromatic ether-based solvents include, but are not limited to, 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1, 2-dimethoxy-4- (1-propenyl) benzene, 1, 4-benzodioxane, 1, 3-dipropylbenzene, 2, 5-dimethoxytoluene, 4-ethylben-ther, 1, 3-dipropoxybenzene, 1,2, 4-trimethoxybenzene, 4- (1-propenyl) -1, 2-dimethoxybenzene, 1, 3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-t-butyl anisole, trans-p-propenyl anisole, 1, 2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, and the like.

In some embodiments, the organic solvent is selected from aliphatic ketone or aliphatic ether based solvents. Aliphatic ketone-based solvents include, but are not limited to, 2-nonene, 3-nonene, 5-nonene, 2-decanone, 2, 5-hexanedione, 2,6, 8-trimethyl-4-nonene, fenchyl ketone, phorone, isophorone, di-n-amyl ketone, and the like, and aliphatic ether-based solvents include, but are not limited to, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, and the like.

In some embodiments, the organic solvent is selected from ester-based solvents. Ester-based solvents include, but are not limited to, alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkyl lactones, alkyl oleates, and the like. Octyl octanoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate are preferred.

In some embodiments, the composition further comprises another organic solvent. The other organic solvent includes at least one of methanol, ethanol, 2-methoxyethanol, methylene chloride, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1, 4-dioxane, acetone, methyl ethyl ketone, 1, 2-dichloroethane, 3-phenoxytoluene, 1-trichloroethane, 1, 2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetrahydronaphthalene, decalin, indene, and the like, but is not limited thereto.

In the present application, the above-mentioned organic solvents may be used alone or in combination of two or more organic solvents.

In some embodiments, the organic solvent of the present application is a solvent having Hansen (Hansen) solubility parameters within the following ranges:

Delta d (dispersion force) is in the range of 17.0-23.2 MPa ^1/2, especially in the range of 18.5-21.0 MPa ^1/2;

δp (polar force) is in the range of 0.2 to 12.5MPa ^1/2, especially in the range of 2.0 to 6.0MPa ^1/2;

δh (hydrogen bonding force) is in the range of 0.9 to 14.2MPa ^1/2, especially in the range of 2.0 to 6.0MPa ^1/2.

The composition according to the application, wherein the organic solvent is selected taking into account its boiling point parameters. In the application, the boiling point of the organic solvent is more than or equal to 150 ℃, preferably more than or equal to 180 ℃, more preferably more than or equal to 200 ℃, more preferably more than or equal to 250 ℃, and most preferably more than or equal to 275 ℃ or more than or equal to 300 ℃. Boiling points in these ranges are beneficial in preventing nozzle clogging of inkjet printheads. The organic solvent may be evaporated from the solvent system to form a film comprising the organic functional material.

In some embodiments, the composition may be a solution.

In some embodiments, the composition may be a suspension.

In some embodiments, the organic compound or the mixture is present in the composition in an amount of 0.01wt% to 10wt%, preferably 0.1wt% to 8wt%, more preferably 0.2wt% to 5wt%, and most preferably 0.25wt% to 3wt%.

In some embodiments, the composition may be used in the preparation of an organic light emitting device as a coating or printing ink, for example by printing or coating.

The printing or coating mode comprises, but is not limited to, ink-jet printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roller printing, offset printing, flexography, rotary printing, spray coating, brush coating or pad printing, slit type extrusion coating and the like. Gravure printing, inkjet printing and ink-jet printing are preferred.

In some embodiments, the composition may further include one or more additional components, such as surface active compounds, lubricants, wetting agents, dispersants, hydrophobing agents, binders, and the like, to adjust the viscosity, film forming properties, adhesion properties, and the like of the composition.

The Organic compound, the mixture and the composition provided by the application can be used for an Organic Light emitting device, which can be, but is not limited to, an Organic electroluminescent element (Organic LIGHT EMITTING Diode, OLED), an Organic photovoltaic cell (Organic Photovoltaics, OPV), an Organic Light-emittingelectrochemicalcells, OLEEC), an Organic field effect transistor (Organic FIELD EFFECT Transistors, OFET), an Organic field effect transistor, an Organic laser, an Organic spintronic device, an Organic sensor, an Organic plasmon emitting Diode (Organic Plasmon Emitting Diode) and the like.

In some embodiments, the organic compound may be applied to an OLED device, and further, the organic compound may be applied to a light emitting layer of an OLED device.

Referring to fig. 1, an embodiment of the present application provides an organic light emitting device 100 including:

A first electrode 120;

A second electrode 140 disposed opposite to the first electrode 120;

an organic functional layer 130 between the first electrode 120 and the second electrode 140;

Wherein the material of the organic functional layer 130 comprises at least one organic compound as described above, or the material of the organic functional layer 130 comprises a mixture as described above.

In some embodiments, the organic functional layer 130 includes at least a light emitting layer 131, the light emitting layer 131 including a host material including the organic compound and a guest material including a compound represented by formula (III):

Wherein,

Ar ³、Ar⁴、Ar⁵、Ar⁶、Ar⁷ is independently selected from at least one of a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 60 ring atoms.

In some embodiments, the Ar ³、Ar⁴、Ar⁵、Ar⁶、Ar⁷ is independently selected from at least one of a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 14 ring atoms.

In some embodiments, the Ar ³、Ar⁴、Ar⁵、Ar⁶、Ar⁷ independently has one of the following structures:

Wherein:

V is selected from CR ₄ or N;

W is selected from NR ₅、CR₅R₆、SiR₅R₆, O, S, S =o or SO ₂;

R ₄、R₅、R₆ is independently selected from the group consisting of-H, -D, straight chain alkyl having 1 to 20C atoms, straight chain alkoxy having 1 to 20C atoms, straight chain thioalkoxy having 1 to 20C atoms, branched alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, CF ₃, cl, br, F, I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 60 heteroatoms.

In some embodiments, R ₄、R₅、R₆ is independently selected from at least one of-H, -D, a straight chain alkyl group having 1 to 10C atoms, a branched alkyl group having 3 to 10C atoms, a cyclic alkyl group having 3 to 10C atoms, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms.

In some embodiments, R ₄、R₅、R₆ is independently selected from-H, -D, a straight chain alkyl group having 1 to 10C atoms, a branched or cyclic alkyl group having 3 to 10C atoms, or phenyl.

In some embodiments, the formula (III) has one of the following structures:

in some embodiments, the formula (III) has one of the following structures:

Referring to fig. 1, a schematic structural diagram of an organic light emitting device according to the present application is shown. The organic light emitting device 100 includes a substrate 110, a first electrode 120 on the substrate, an organic functional layer 130 on a side of the first electrode 120 away from the substrate 110, and a second electrode 140 on a side of the organic functional layer 130 away from the first electrode 120. The organic light emitting device 100 may be an OLED device, but is not limited thereto.

The substrate 110 may be a transparent substrate or an opaque substrate, and when the substrate 110 is a transparent substrate, a transparent organic light emitting device may be fabricated, and the substrate 110 may be a rigid substrate or a flexible substrate with elasticity, and the material of the substrate 110 may include, but is not limited to, plastics, polymers, metals, semiconductor wafers, glass, or the like. Preferably, the substrate 110 includes at least one smooth surface to form the first electrode 120 on the surface, and more preferably, the surface is free of surface defects. Preferably, the material of the substrate 110 is a polymer film or plastic, including but not limited to polyethylene terephthalate (PET material) and polyethylene glycol (2, 6-naphthalene) (PEN material), and the glass transition temperature of the substrate 110 is greater than or equal to 150 ℃, preferably greater than or equal to200 ℃, more preferably greater than or equal to 250 ℃, and most preferably greater than or equal to 300 ℃.

The first electrode 120 may be an anode, which is an electrode injecting holes, and the anode may inject holes into the organic functional layer, for example, the anode injects holes into the hole injection layer, the hole transport layer, or the light emitting layer. The anode may include at least one of a conductive metal, a conductive metal oxide, or a conductive polymer. Preferably, the absolute value of the difference between the work function of the anode and the energy level or valence band of the light emitting material in the light emitting layer or the HOMO (highest occupied molecular orbital ) as p-type semiconductor material in the hole injection layer or hole transport layer or electron blocking layer is less than 0.5eV, preferably less than 0.3eV, more preferably less than 0.2eV. The anode material includes, but is not limited to, at least one of Al, cu, au, ag, mg, fe, co, ni, mn, pd, pt, ITO (Indium Tin Oxide), aluminum doped zinc Oxide (AZO), etc., or other suitable and known anode materials, which can be readily selected by one of ordinary skill in the art. The material of the anode may be deposited using any suitable technique, such as a suitable physical vapor deposition method including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like. In some embodiments, the anode is patternable, e.g., a patterned ITO conductive substrate is commercially available and can be used to make the organic light emitting device of the present application.

The second electrode 140 may be a cathode, which is an electrode injecting electrons, and the cathode may inject electrons into the organic functional layer, such as the electron injection layer, the electron transport layer, or the light emitting layer. The cathode may include at least one of a conductive metal or a conductive metal oxide. Preferably, the absolute value of the difference between the work function of the cathode and the LUMO (lowest unoccupied molecular orbital ) level or conduction band level of the light-emitting material in the light-emitting layer or the n-type semiconductor material as an electron injection layer or electron transport layer or hole blocking layer is less than 0.5eV, preferably less than 0.3eV, more preferably less than 0.2eV. All materials that can be used as cathodes for the organic light emitting devices are possible as cathode materials for the devices of the present application, including but not limited to at least one of Al, au, ag, ca, ba, mg, liF/Al, mgAg alloy, baF ₂/Al, cu, fe, co, ni, mn, pd, pt, ITO, etc. The material of the cathode may be deposited using any suitable technique, such as a suitable physical vapor deposition method including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.

The organic functional layer 130 includes a light emitting layer 131, and the light emitting layer 131 includes an organic compound as described above. The organic functional layer 130 may further include other functional layers such as a Hole Injection Layer (HIL) 132, a Hole Transport Layer (HTL) 133, an Electron Blocking Layer (EBL), an Electron Injection Layer (EIL), an Electron Transport Layer (ETL) 134, and a Hole Blocking Layer (HBL). Detailed descriptions of various organic functional materials included in the organic functional layer 130 are detailed in WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are hereby incorporated by reference.

In some embodiments, the organic light emitting device 100 may be a solution type OLED.

In some embodiments, the organic light emitting device 100 emits light having a wavelength between 300 and 1000nm, further, the organic light emitting device 100 emits light having a wavelength between 350 and 900nm, still further, the organic light emitting device 100 emits light having a wavelength between 400 and 800nm, and still further, the organic light emitting device 100 emits light having a wavelength in the blue light wavelength range.

The organic light emitting device 100 of the present application may be applied to various electronic devices including, but not limited to, display devices, lighting devices, light sources, sensors, etc.

The organic compound and the organic light emitting device according to the present application will be further described with reference to specific examples.

1. Synthesis of organic Compounds

Example 1

Synthesis of Compound M1

Synthesis of intermediate 1-3:

Intermediate 1-1 (10 mmol), 1-2 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin to remove most of the solvent, then extracted and water washed to separate the liquid, the organic phase was chromatographed and recrystallized to give intermediate 1-3 in a molar amount of 9.27mmol and a yield of 92.7%. Atmospheric solid phase analytical probe mass spectrometry (ASAP-MS) of intermediate 1-3 gave MS (ASAP) =383.

Synthesis of compound M1:

Intermediate 1-3 (10 mmol) and 1-4 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin to remove most of the solvent, then extracted and water washed to separate the liquid, and the organic phase was chromatographed and recrystallized to give compound M1 in a molar amount of 7.89mmol and a yield of 78.9%. Atmospheric solid phase analysis probe mass spectrometry (ASAP-MS) result of compound M1: MS (ASAP) =525.

Example 2

Synthesis of Compound M2

Synthesis of intermediate 2-1:

Intermediate 1-3 (10 mmol), 1-2 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin to remove most of the solvent, then extracted and water washed to separate the liquid, the organic phase was chromatographed and recrystallized to give intermediate 2-2 in a molar amount of 8.33mmol and a yield of 83.3%. Atmospheric solid phase analysis probe mass spectrometry (ASAP-MS) of intermediate 2-1 gave MS (ASAP) =473.

Synthesis of compound M2:

Intermediate 2-1 (10 mmol) and 1-4 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin to remove most of the solvent, then extracted and water washed to separate the liquid, and the organic phase was chromatographed and recrystallized to give compound M2 in a molar amount of 7.32mmol and a yield of 73.2%. Atmospheric solid phase analysis probe mass spectrometry (ASAP-MS) result of compound M2: MS (ASAP) =615.

Example 3

Synthesis of Compound M3

Synthesis of intermediate 3-3:

Intermediate 3-1 (10 mmol), 3-2 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin to remove most of the solvent, then extracted and water washed to separate the liquid, the organic phase was chromatographed and recrystallized to give intermediate 3-3 in a molar amount of 8.21mmol, yield 82.1%. Atmospheric solid phase analytical probe mass spectrometry (ASAP-MS) results of intermediate 3-3: MS (ASAP) =419.

Synthesis of compound M3:

Intermediate 3-3 (10 mmol) and 1-4 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin to remove most of the solvent, then extracted and water washed to separate the liquid, and the organic phase was chromatographed and recrystallized to give compound M3 in a molar amount of 7.56mmol and a yield of 75.6%. Atmospheric solid phase analysis probe mass spectrometry (ASAP-MS) result of compound M3: MS (ASAP) =561.

Example 4

Synthesis of Compound M4

Synthesis of intermediate 4-2:

Intermediate 1-1 (10 mmol), 4-1 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin to remove most of the solvent, then extracted and water washed to separate the liquid, the organic phase was chromatographed and recrystallized to give intermediate 4-2 in a molar amount of 6.74mmol and a yield of 67.4%. Atmospheric solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 4-2: MS (ASAP) =463.

Synthesis of compound M4:

Intermediate 4-2 (10 mmol), 1-4 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin to remove most of the solvent, then extracted and water washed to separate the liquid, and the organic phase was chromatographed and recrystallized to give compound M4 in a molar amount of 7.15mmol and a yield of 71.5%. As a result of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of compound M4 MS (ASAP) =561.

Example 5

Synthesis of Compound M5

Synthesis of intermediate 5-1:

intermediate 4-2 (10 mmol), 4-1 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin-evaporation to remove most of the solvent, then extracted and washed with water to give intermediate 5-1 by organic phase column chromatography and recrystallisation in an molar amount of 8.36mmol, yield 83.6% as a result of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of intermediate 5-1, MS (ASAP) =589.

Synthesis of compound M5:

Intermediate 5-1 (10 mmol) and 1-4 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin to remove most of the solvent, then extracted and water washed to separate the liquid, and the organic phase was chromatographed and recrystallized to give compound M5 in a molar amount of 7.24mmol and a yield of 72.4%. Atmospheric solid phase analysis probe mass spectrometry (ASAP-MS) result of compound M5: MS (ASAP) =687.

Example 6

Synthesis of Compound M6

Synthesis of intermediate 6-2:

Intermediate 1-1 (10 mmol), 6-1 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin to remove most of the solvent, then extracted and water washed to separate the liquid, the organic phase was chromatographed and recrystallized to give intermediate 6-2 in 5.33mmol, 53.3% yield as a result of atmospheric solid phase analytical probe mass spectrometry (ASAP-MS) of intermediate 6-2, MS (ASAP) =563.

Synthesis of compound M6:

intermediate 6-2 (10 mmol), 1-4 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin to remove most of the solvent, then extracted and water washed to separate the liquid, and the organic phase was chromatographed and recrystallized to give compound M6 in a molar amount of 6.79mmol and a yield of 67.9%. Atmospheric solid phase analysis probe mass spectrometry (ASAP-MS) result of compound M6: MS (ASAP) =661.

Example 7

Synthesis of Compound M7

Synthesis of intermediate 7-2:

Intermediate 1-1 (10 mmol), 7-1 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin to remove most of the solvent, then extracted and water washed to separate the liquid, the organic phase was chromatographed and recrystallized to give intermediate 7-2 in a molar amount of 7.38mmol and a yield of 73.8%. Atmospheric solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 7-2: MS (ASAP) =463.

Synthesis of compound M7:

Intermediate 7-2 (10 mmol), 1-4 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin to remove most of the solvent, then extracted and water washed to separate the liquid, and the organic phase was chromatographed and recrystallized to give compound M7 in a molar amount of 7.56mmol and a yield of 75.6%. Atmospheric solid phase analysis probe mass spectrometry (ASAP-MS) result of compound M7: MS (ASAP) =561.

Example 8

Synthesis of Compound M8

Synthesis of intermediate 8-2:

Intermediate 1-1 (10 mmol), 8-1 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin-evaporation to remove most of the solvent, then extracted and water washed to separate the liquid, the organic phase was chromatographed and recrystallized to give intermediate 8-2 in a molar amount of 7.87mmol and a yield of 78.7%. Atmospheric solid phase analytical probe mass spectrometry (ASAP-MS) of intermediate 8-2 gave MS (ASAP) =513.

Synthesis of compound M8:

Intermediate 8-2 (10 mmol) and 8-3 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin to remove most of the solvent, then extracted and water washed to separate the liquid, and the organic phase was chromatographed and recrystallized to give compound M8 in a molar amount of 8.13mmol and a yield of 81.3%. Atmospheric solid phase analysis probe mass spectrometry (ASAP-MS) of compound M8 gave MS (ASAP) =611.

Example 9

Synthesis of Compound M9

Synthesis of intermediate 9-2:

Intermediate 8-2 (10 mmol), 9-1 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin-evaporation to remove most of the solvent, then extracted and water washed to separate the liquid, the organic phase was chromatographed and recrystallized to give intermediate 9-2 in a molar amount of 8.21mmol, yield 82.1%. Atmospheric solid phase analysis probe mass spectrometry (ASAP-MS) results of intermediate 9-2 MS (ASAP) =603.

Synthesis of compound M9:

intermediate 9-2 (10 mmol), 1-4 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin to remove most of the solvent, then extracted and water washed to separate the liquid, and the organic phase was chromatographed and recrystallized to give compound M9 in a molar amount of 7.59mmol and a yield of 75.9% as a result of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of compound M9 MS (ASAP) =701.

Example 10

Synthesis of Compound M10

Synthesis of intermediate 10-1:

Intermediate 1-4 (10 mmol), 7-1 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin to remove most of the solvent, then extracted and water washed to separate the liquid, and the organic phase was chromatographed and recrystallized to give intermediate 10-1 in a molar amount of 6.37mmol and a yield of 63.7%. Atmospheric solid phase analysis probe mass spectrometry (ASAP-MS) of intermediate 10-1 gave MS (ASAP) =348.

Synthesis of compound M10:

Intermediate 10-1 (10 mmol), 7-2 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin to remove most of the solvent, then extracted and water washed to separate the liquid, and the organic phase was chromatographed and recrystallized to give compound M10 in a molar amount of 8.46mmol with a yield of 84.6%. Atmospheric solid phase analysis probe mass spectrometry (ASAP-MS) of compound M10 gave MS (ASAP) =687.

Example 11

Synthesis of Compound M11

Synthesis of intermediate 11-2:

Intermediate 10-1 (10 mmol), 11-1 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin-evaporation to remove most of the solvent, then extracted and washed with water to give intermediate 11-2 in an molar amount of 8.17mmol and yield of 81.7% by mass spectrometry (ASAP-MS) of intermediate 11-2 as a result of MS (ASAP) =474.

Synthesis of compound M11:

Intermediate 11-2 (10 mmol), 1-1 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin to remove most of the solvent, then extracted and water washed to separate the liquid, and the organic phase was chromatographed and recrystallized to give compound M11 in a molar amount of 7.84mmol and a yield of 78.4%. Atmospheric solid phase analysis probe mass spectrometry (ASAP-MS) of compound M11 gave MS (ASAP) =687.

Example 12

Synthesis of Compound M12

Synthesis of intermediate 12-1:

Intermediate 7-2 (10 mmol), 11-1 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin-evaporation to remove most of the solvent, then extracted and water washed to separate the liquid, and the organic phase was chromatographed and recrystallized to give intermediate 12-1 in a molar amount of 7.41mmol and a yield of 74.1%. Atmospheric solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 12-1: MS (ASAP) =589.

Synthesis of compound M12:

Intermediate 12-1 (10 mmol), 1-4 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin to remove most of the solvent, then extracted and water washed to separate the liquid, and the organic phase was chromatographed and recrystallized to give compound M12 in a molar amount of 7.96mmol and a yield of 79.6%. Atmospheric solid phase analysis probe mass spectrometry (ASAP-MS) of compound M12 gave MS (ASAP) =687.

Example 13

Synthesis of Compound M13

Synthesis of intermediate 13-2:

Intermediate 1-1 (10 mmol), 13-1 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin-evaporation to remove most of the solvent, then extracted and water washed to separate the liquid, the organic phase was chromatographed and recrystallized to give intermediate 13-2 in a molar amount of 7.56mmol and a yield of 75.6%. Atmospheric solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 13-2: MS (ASAP) =463.

Synthesis of compound M13:

Intermediate 3-2 (10 mmol) and 1-4 (10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (21/2 ml), pd (PPh ₃)₄ (0.1 mmol) and potassium carbonate (30 mmol) were added, stirred under nitrogen atmosphere at 100℃for 6h, cooled, evaporated off by spin to remove most of the solvent, then extracted and water washed to separate the liquid, and the organic phase was chromatographed and recrystallized to give compound M13 in a molar amount of 7.17mmol and a yield of 71.7%. As a result of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of compound M13, MS (ASAP) =561.

Comparative example 1

The organic compound adopted by the comparative compound 1 is BH-ref-1, and the structure of BH-ref-1 is as follows:

comparative example 2

The organic compound adopted by the comparative compound 1 is BH-ref-2, and the structure of BH-ref-2 is as follows:

2. Preparation and characterization of organic light emitting devices

(1) The compounds M1 to M13 obtained in examples 1 to 13 and the comparative compound 1 in comparative example 1, the HOMO (Highest Occupied Molecular Orbital ) energy level, LUMO (Lowest Unoccupied Molecular Orbital, lowest unoccupied molecular orbital) energy level, T1 (first excited triplet) energy level, S1 (first excited singlet) energy level of the comparative compound 2 in comparative example 2 can be obtained by quantum computation. The TD-DFT (time-Density functional theory) method can be used by Gaussian09W (Gaussian Inc.), and specific simulation methods can be found in WO2011141110. The molecular geometry is first optimized by the Semi-empirical method "group State/Semi-empirical/Default Spin/AM1" (Charge 0/SPIN SINGLET), and then the energy structure of the organic molecule is calculated by the TD-DFT (time-Density functional theory) method to "TD-SCF/DFT/Default Spin/B3PW91" and the basis set "6-31G (d)" (Charge 0/SPIN SINGLET). The HOMO and LUMO energy levels are calculated according to the following calibration formula, and S1, T1 and resonance factor f (S1) are directly used.

HOMO(eV)=((HOMO(G)×27.212)-0.9899)/1.1206;

LUMO(eV)=((LUMO(G)×27.212)-2.0041)/1.385;

Wherein HOMO, LUMO, T and S1 are direct calculations of Gaussian 09W in Hartree.

The energy level results of the organic compounds M1 to M13 and the comparative compounds 1, 2 are shown in table 1 below:

TABLE 1 organic Compound energy level data sheet

(2) Preparation of organic light-emitting device

The structure of the organic light emitting device 100 prepared in this embodiment, including the substrate 110, the first electrode (anode) 120, the Hole Injection Layer (HIL) 132, the Hole Transport Layer (HTL) 133, the light emitting layer 131, the Electron Transport Layer (ETL) 134, and the second electrode (cathode) 140, which are sequentially stacked, is referred to as fig. 1. In this embodiment, the organic light emitting device 100 is an OLED, and is a blue light emitting device.

The preparation steps of the organic light emitting device are as follows:

a. cleaning ITO (indium tin oxide) conductive glass, namely cleaning the ITO conductive glass by using a solvent (such as one or more of chloroform, acetone or isopropanol), and then performing ultraviolet ozone treatment, wherein the ITO conductive glass comprises a substrate and an anode formed on the substrate;

b. Forming a hole injection layer by spin-coating a material PEDOT (polyethylene dioxythiophene, clevelos ^TM AI 4083) of the hole injection layer on an ITO anode in an ultra clean room, and processing on a hot plate at 180 ℃ for 10 minutes, wherein the thickness of the formed hole injection layer is 40nm;

c. Forming a hole transport layer by spin-coating a toluene solution of TFB or PVK (SIGMA ALDRICH, mn 25,000-50,000) at a concentration of 5mg/ml on the hole injection layer in a nitrogen glove box, followed by treatment on a hot plate at 180℃for 60 minutes, the thickness of the formed hole transport layer being 20nm;

d. and forming a light-emitting layer, namely spin-coating a light-emitting layer material on the hole-transporting layer in a nitrogen glove box, then processing the light-emitting layer material on a hot plate at 140 ℃ for 10 minutes, wherein host materials in the light-emitting layers of different organic light-emitting devices respectively correspond to one of the compounds M1 to M13, guest materials in the light-emitting layers of different organic light-emitting devices are BD-1, a solvent is methyl benzoate solution, the mass ratio of the host materials to the guest materials is 95:5, the concentration of the materials of the light-emitting layer is 15mg/ml, and the thickness of the finally formed light-emitting layer is 40nm.

E. Forming an electron transport layer, namely placing ET and Liq on different evaporation units in a vacuum cavity above the light-emitting layer, and codeposition the ET and the Liq in a mass ratio of 50:50 under a high vacuum (1X 10-6 mbar) environment to form the electron transport layer with the thickness of 20 nm;

f. forming a cathode layer, namely depositing Al on the electron transport layer to obtain an Al cathode with the thickness of 100 nm;

g. And (5) packaging, namely packaging the device obtained in the step f by ultraviolet curing resin in a nitrogen glove box.

In the present embodiment, the organic light emitting devices 1 to 13 and the comparative elements 1 and 2 were obtained through the above steps. Wherein the host materials used in the organic light emitting devices 1 to 13 are the organic compounds M1 to M13, the guest materials used in the organic light emitting devices 1 to 13 are BD-1, the host materials used in the contrast elements 1 and 3 are the contrast compounds 1 and 2, and the guest materials used in the contrast elements 1 and 2 are BD-1.

Wherein ET, liq, BD-1 has the structure as follows:

The organic light emitting devices 1 to 13 and the comparative elements 1 and 2 prepared as described above were subjected to a current-voltage (J-V) characteristic test, and CIE color coordinates (x, y) of each organic light emitting device and comparative element, a driving voltage (voltage @1knits [ V ]), a luminous efficiency (ce @1knits [ cd/a ]) at a current density of 10mA/cm ², and a time (lt 90@1knits [ h ]) for which the luminance was reduced from the initial luminance of 1knits to 90% of the initial luminance were obtained, and the specific results are shown in table 2.

Table 2 performance data of organic light emitting devices

As can be seen from the above data, the color coordinates of the blue organic light emitting devices 1 to 13 prepared by using the compounds M1 to M13 as the host materials in the light emitting layer according to the present application are better than those of the comparative elements 1 and 2 prepared by using the comparative compounds 1 and 2 as the host materials in the light emitting layer.

As is apparent from the above data, the light-emitting efficiency of the organic light-emitting devices 1 to 13 prepared using the compounds M1 to M13 as the host materials in the light-emitting layer is in the range of 8.6 to 9.4cd/a, which is far greater than the light-emitting efficiency of the comparative elements 1 and 2 prepared using the comparative compounds 1 and 2 as the host materials in the light-emitting layer, and thus, the organic light-emitting devices using the organic compounds of the present application have more excellent light-emitting efficiency.

Among them, the performance of the organic light emitting devices 7, 8, 9, 13 is superior to that of the comparative element 1 because the organic light emitting device performance is improved by introducing 2 anthracene groups (compounds M8, M9) or 1 naphthalene and 1 anthracene group (compounds M7, M13) between phenanthrene and anthracene, which can promote the conjugation of molecules, than the comparative element 1 by introducing 1 anthracene group (BH-ref-1), and the device performance is deteriorated by introducing 2 anthracene groups or 1 naphthalene and 1 anthracene group between phenanthrene and anthracene, which can deteriorate the intermolecular conjugation thereof in the comparative compound 1. The performance of the organic light-emitting devices 1 to 13 is superior to that of the comparative element 2 because the compound M1 to M13 has aromatic ring groups (such as benzene, naphthalene, anthracene, etc.) with conjugated structures, which are mostly introduced between phenanthrene and anthracene, so that the molecular weight of the organic compound is increased, the conjugation of the organic compound molecules is also increased, and the thermal stability of the organic compound molecules is improved, so that the light-emitting efficiency and the service life of the organic light-emitting devices 1 to 13 prepared by using the compound M1 to M13 as a blue light host material in a light-emitting layer are obviously improved.

The organic compound, the mixture, the composition and the organic light emitting device provided by the embodiments of the present application are described in detail, and specific examples are used herein to illustrate the principles and embodiments of the present application, and the description of the above embodiments is only for aiding in understanding the technical solutions and core ideas of the present application, and those of ordinary skill in the art should understand that they may still modify the technical solutions described in the foregoing embodiments or make equivalent substitutions for some of the technical features thereof, and these modifications or substitutions do not make the essence of the corresponding technical solutions deviate from the scope of the technical solutions of the embodiments of the present application.

Claims (12)

1. An organic compound, characterized in that the organic compound has a structure represented by formula (I):

Wherein,

N1 is 0, 1 or 2, n2 is 0, 1 or 2, and n1, n2 are not simultaneously 0;

Ar ¹ and Ar ² independently have one of the following structures:

Wherein,

X is selected from CR ₁ or N;

Y is selected from NR ₂、CR₂R₃、SiR₂R₃, O, S, S =o or SO ₂;

R ₁、R₂、R₃ is independently selected from the group consisting of-H, -D, straight chain alkyl having 1 to 20C atoms, straight chain alkoxy having 1 to 20C atoms, straight chain thioalkoxy having 1 to 20C atoms, branched alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, CF ₃, cl, br, F, I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 60 heteroatoms;

when Ar ¹ and Ar ² are independently selected from benzene rings, R ₁ on the benzene rings are not simultaneously H.

2. The organic compound of claim 1, wherein Ar ¹ and Ar ² independently have one of the following structures:

Wherein, represents the site of attachment.

3. The organic compound according to claim 2, wherein Ar ¹ and Ar ² independently have one of the structures represented by A1 to A7:

4. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of compounds represented by formulas II-1 to II-10:

5. The organic compound according to claim 4, wherein R ₁ is selected from-H, -D, straight chain alkyl having 1 to 10C atoms, branched alkyl having 3 to 10C atoms, cyclic alkyl having 3 to 10C atoms, or phenyl.

6. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of compounds represented by the following structures:

7. A mixture comprising at least one organic compound according to any one of claims 1 to 6 and at least one organic functional material selected from a hole injecting material, a hole transporting material, an electron injecting material, an electron blocking material, a hole blocking material, a light emitting material, a host material or an organic dye.

8. A composition comprising at least one organic compound according to any one of claims 1 to 6 and at least one organic solvent, or comprising the mixture according to claim 7 and at least one of said organic solvents.

9. An organic light emitting device, comprising:

a first electrode;

A second electrode disposed opposite to the first electrode, and

An organic functional layer between the first electrode and the second electrode;

Wherein the material of the organic functional layer comprises at least one organic compound according to any one of claims 1 to 6, or the material of the organic functional layer comprises a mixture according to claim 7.

10. The organic light-emitting device according to claim 9, wherein the organic functional layer includes at least a light-emitting layer, the light-emitting layer includes a host material including the organic compound and a guest material including a compound represented by formula (III):

Wherein,

Ar ³、Ar⁴、Ar⁵、Ar⁶、Ar⁷ is independently selected from at least one of a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 60 ring atoms.

11. The organic light-emitting device according to claim 10, wherein Ar ³、Ar⁴、Ar⁵、Ar⁶、Ar⁷ independently has one of the following structures:

Wherein:

V is selected from CR ₄ or N;

W is selected from NR ₅、CR₅R₆、SiR₅R₆, O, S, S =o or SO ₂;

R ₄、R₅、R₆ is independently selected from the group consisting of-H, -D, straight chain alkyl having 1 to 20C atoms, straight chain alkoxy having 1 to 20C atoms, straight chain thioalkoxy having 1 to 20C atoms, branched alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, CF ₃, cl, br, F, I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 60 heteroatoms.

12. The organic light-emitting device according to claim 10, wherein the formula (III) has one of the following structures: