CN107619391A

CN107619391A - Heterocyclic compound and the organic luminescent device including the heterocyclic compound

Info

Publication number: CN107619391A
Application number: CN201710570054.5A
Authority: CN
Inventors: 沈文基; 朴俊河; 李孝荣; 郑恩在; 金荣国; 黄晳焕
Original assignee: Samsung Display Co Ltd
Current assignee: Samsung Display Co Ltd
Priority date: 2016-07-13
Filing date: 2017-07-13
Publication date: 2018-01-23
Anticipated expiration: 2037-07-13
Also published as: KR20180008293A; CN107619391B; KR102460644B1

Abstract

Provide a kind of heterocyclic compound and the organic luminescent device including the heterocyclic compound, the heterocyclic compound by<Formula 1>Represent：

Description

Heterocyclic compound and the organic luminescent device including the heterocyclic compound

This application claims entitled " Heterocyclic Compound and Organic Light-Emitting Device Including the Same (heterocyclic compound and the organic luminescent device including the heterocyclic compound) " in 10-2016-0088703 korean patent applications that on July 13rd, 2016 submits in Korean Intellectual Property Office and in 2017 7 The priority and rights and interests for the 10-2017-0084990 korean patent applications that the moon 4 was submitted in Korean Intellectual Property Office, this two This is incorporated herein by reference in all the elements of part korean patent application.

Technical field

Embodiment is related to a kind of heterocyclic compound and the organic luminescent device including the heterocyclic compound.

Background technology

Organic luminescent device is spontaneous emission device, has wide viewing angle, high-contrast, short response time and excellent bright Degree, driving voltage and response speed characteristic, and produce full-colour image.The example of such organic luminescent device can include setting First electrode in substrate and the hole transporting zone being sequentially positioned in first electrode, emission layer, electric transmission area Domain and second electrode.It can pass through hole transporting zone from the hole that first electrode provides to move towards emission layer, from the second electricity The electronics that pole provides can move by electron transporting zone towards emission layer.The carrier in such as hole and electronics is in emission layer In it is compound to produce exciton.These excitons transit to ground state from excitation state, so as to produce light.

The content of the invention

Embodiment is related to a kind of heterocyclic compound represented by formula 1：

*-(L₁₁)_a11-(R₁₂)_b12,

Wherein, next further limitation type 1 as set forth herein and formula 2.

According to one or more embodiments, organic luminescent device includes：First electrode；Second electrode, in face of the first electricity Pole；And organic layer, it is arranged between first electrode and second electrode, and including emission layer, wherein, organic layer is included by formula 1 The heterocyclic compound of expression.

Brief description of the drawings

Exemplary embodiment is described in detail by referring to accompanying drawing, feature is for those skilled in the art It will be apparent, in the accompanying drawings：

Fig. 1 shows the schematic diagram of the organic luminescent device according to embodiment；

Fig. 2 shows the schematic diagram of the organic luminescent device according to embodiment；

Fig. 3 shows the schematic diagram of the organic luminescent device according to embodiment；And

Fig. 4 shows the schematic diagram of the organic luminescent device according to embodiment.

Embodiment

Example embodiment is described more fully hereinafter with reference to accompanying drawing now；However, example embodiment can be with Different forms is implemented, and should not be construed as being limited to the embodiment illustrated herein.Conversely, there is provided these implementations Example so that the disclosure will be the thoroughly and completely and technology that illustrative embodiments will be fully conveyed to this area Personnel.In the accompanying drawings, for clear explanation, the size in layer and region can be exaggerated.Same reference represents same all the time Element.

It can be represented according to the heterocyclic compound of embodiment by formula 1：

*-(L₁₁)_a11-(R₁₂)_b12,

Wherein, the R in formula 1 and formula 2₁To R₁₁、L₁₁、a11、R₁₂With b12 with it is described below identical.

In formula 1,

R₅Can be the group represented by formula 2, and

R₁To R₄And R₆To R₁₁Can be independently selected from the group, hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, the hydroxyl that are represented by formula 2 Base, cyano group, nitro, amidino groups, diazanyl, hydrazone group, substituted or unsubstituted C₁-C₆₀Alkyl, substituted or unsubstituted C₂-C₆₀Alkenyl, Substituted or unsubstituted C₂-C₆₀Alkynyl, substituted or unsubstituted C₁-C₆₀Alkoxy, substituted or unsubstituted C₃-C₁₀Cycloalkyl, Substituted or unsubstituted C₁-C₁₀Heterocyclylalkyl, substituted or unsubstituted C₃-C₁₀Cycloalkenyl group, substituted or unsubstituted C₁-C₁₀Heterocycle Alkenyl, substituted or unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₆-C₆₀Aryloxy group, substituted or unsubstituted C₆-C₆₀Virtue Sulfenyl, substituted or unsubstituted C₁-C₆₀Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensation polycyclic base, substitution do not take The monovalent non-aromatic in generation is condensed miscellaneous more ring groups ,-N (Q₁)(Q₂)、-Si(Q₁)(Q₂)(Q₃) and-B (Q₁)(Q₂), but embodiment is not It is limited to this.

In one or more embodiments, the R in formula 1₁To R₄And R₆To R₁₁Can independently selected from：

The group represented by formula 2；

Hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkyl and C₁-C₂₀Alkane Epoxide；

Phenyl, xenyl, terphenyl, pentalene base, indenyl, naphthyl, camomile ring group, heptalene base, indacene Base, acenaphthenyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, that non-alkenyl, phenanthryl, anthryl, fluoranthene base, benzo [9, 10] phenanthryl, pyrenyl,Base, aphthacene Ji, Pi base, base, pentaphene base, hexacene base, pentacene base, rubicene Ji, guans base, Ovalene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofurans Base, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene cough up base and pyridine radicals；

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkane Base, C₁-C₂₀Alkoxy, cyclopenta, cyclohexyl, suberyl, cyclopentenyl, cyclohexenyl group, phenyl, xenyl, terphenyl, take , there is C in generation₁-C₁₀The phenyl of alkyl, substitution have-F phenyl, pentalene base, indenyl, naphthyl, camomile ring group, heptalene base, Indacene base, acenaphthenyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, that non-alkenyl, phenanthryl, anthryl, fluoranthene base, benzene And [9,10] phenanthryl, pyrenyl,Base, aphthacene Ji, Pi base, base, pentaphene base, hexacene base, pentacene base, rubicene base, Guan base, ovalene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzo Furyl, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene cough up base, pyridine radicals ,-Si (Q₃₁)(Q₃₂) (Q₃₃) and-N (Q₃₁)(Q₃₂) at least one of phenyl, xenyl, terphenyl, pentalene base, indenyl, naphthyl, sweet Chrysanthemum ring group, heptalene base, indacene base, acenaphthenyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, that non-alkenyl, phenanthrene Base, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, aphthacene Ji, Pi base, base, pentaphene base, hexacene base, Pentacene base, rubicene Ji, guans base, ovalene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzofuran Base, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene cough up base And pyridine radicals；And

-Si(Q₁)(Q₂)(Q₃),

Wherein, Q₁To Q₃And Q₃₁To Q₃₃Can independently selected from：

C₁-C₁₀Alkyl, C₁-C₁₀Alkoxy, phenyl, xenyl, terphenyl, naphthyl, pyridine radicals, pyrimidine radicals, pyrazinyl, Quinolyl, isoquinolyl, quinoxalinyl and quinazolyl；And

Substitution has selected from C₁-C₁₀Alkyl, C₁-C₁₀The phenyl of at least one of alkoxy and phenyl, xenyl, three Xenyl, naphthyl, pyridine radicals, pyrimidine radicals, pyrazinyl, quinolyl, isoquinolyl, quinoxalinyl and quinazolyl,

But embodiment not limited to this.

The group represented by formula 2；

Substitution has in deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl and hydrazone group at least The C of one₁-C₂₀Alkyl and C₁-C₂₀Alkoxy；

Cyclopenta, cyclohexyl, cyclopentenyl, cyclohexenyl group, phenyl, xenyl and terphenyl；

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkane Base, C₁-C₂₀In alkoxy, cyclopenta, cyclohexyl, cyclopentenyl, cyclohexenyl group, phenyl, xenyl and terphenyl at least Cyclopenta, cyclohexyl, cyclopentenyl, cyclohexenyl group, phenyl, xenyl and the terphenyl of one；And

-Si(Q₁)(Q₂)(Q₃),

Wherein, Q₁To Q₃Can be independently selected from C₁-C₂₀Alkyl, C₁-C₂₀Alkoxy, phenyl and naphthyl, but implement Example not limited to this.

L in formula 2₁₁Substituted or unsubstituted C can be selected from₃-C₁₀Cycloalkylidene, substituted or unsubstituted C₁-C₁₀It is sub- Heterocyclylalkyl, substituted or unsubstituted C₃-C₁₀Sub- cycloalkenyl group, substituted or unsubstituted C₁-C₁₀Sub- heterocycloalkenyl, substitution do not take The C in generation₆-C₆₀Arlydene, substituted or unsubstituted C₁-C₆₀Inferior heteroaryl, the non-aromatic condensation polycyclic of substituted or unsubstituted divalence The miscellaneous more ring groups of the non-aromatic condensation of base, substituted or unsubstituted divalence, *-P (=O) (Q₄)-* ', *-P (=S) (Q₄)-* ', *-S (= O)-* ' and *-S (=O)₂- * ', but embodiment not limited to this.

In one or more embodiments, the L in formula 2₁₁It can be selected from：

Phenylene, sub- pentalene base, sub-indenyl, naphthylene, sub- camomile ring group, sub- indacene base, sub- acenaphthenyl, sub- fluorenes Base, the fluorenyl of sub- spiral shell two, sub- spiral shell benzfluorene-fluorenyl, sub- benzo fluorenyl, sub- dibenzo fluorenyl, that alkenyl of Asia and Africa, phenanthrylene, sub- anthracene Base, sub- fluoranthene base, sub- benzo [9,10] phenanthryl, sub- pyrenyl, AsiaBase, subunit, sub- pentacene base, sub- pyrrole radicals, sub- thiophene Base, furylidene, sub- thiophene cough up base, sub- imidazole radicals, sub- pyrazolyl, sub- thiazolyl, sub- isothiazolyl, Ya oxazolyls, Ya isoxazoles Base, sub- pyridine radicals, sub- pyrazinyl, sub- pyrimidine radicals, sub- pyridazinyl, sub- indyl, sub- isoindolyl, sub- indazolyl, sub- purine radicals, Sub- quinolyl, sub- isoquinolyl, sub- benzoquinoline base, sub- benzisoquinoline base, sub- phthalazinyl, sub- naphthyridines base, sub- quinoxalinyl, Sub- quinazolyl, sub- cinnolines base, sub- phenanthridinyl, sub- acridinyl, sub- phenanthroline, sub- phenazinyl, sub- benzimidazolyl, sub- benzo Furyl, sub- benzothienyl, sub- benzo thiophene cough up base, sub- benzothiazolyl, sub- different benzothiazolyl, sub- benzoxazolyl, Asia Yi benzoxazolyls, sub- triazolyl, sub- tetrazole radical, Ya oxadiazolyls, sub- triazine radical, sub- carbazyl, sub- dibenzofuran group, Asia Dibenzothiophenes base, sub- dibenzo thiophene cough up base, sub- benzo carbazole base, sub- naphtho- benzofuranyl, sub- naphtho- benzothienyl, Asia Naphtho- benzo thiophene coughs up base, sub- dibenzo-carbazole base, sub- dinaphtho furyl, sub- dinaphtho thienyl, sub- dinaphtho thiophene and coughs up base, Asia Thiadiazolyl group, sub- imidazopyridyl, sub- imidazopyrimidine base, Ya oxazoles and pyridine radicals, sub- thiazolopyridinyl, sub- benzo naphthalene Piperidinyl, sub- azepine fluorenyl, the fluorenyl of sub- azaspiro two, sub- azepine carbazyl, sub- azepine dibenzofuran group, sub- azepine dibenzo thiophene Fen base, sub- azepine dibenzo thiophene cough up base, sub- indeno-pyrrole base, sub- indoles and pyrrole radicals, sub- indeno carbazyl and sub- indoles and click Oxazolyl；And

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkane Base, C₁-C₂₀Alkoxy, C₃-C₁₀Cycloalkyl, C₁-C₁₀Heterocyclylalkyl, C₃-C₁₀Cycloalkenyl group, C₁-C₁₀Heterocycloalkenyl, C₆-C₂₀Aryl, C₁-C₂₀Heteroaryl, monovalent non-aromatic condensation polycyclic base, monovalent non-aromatic are condensed miscellaneous more ring groups, aminomethyl phenyl, xenyl and-Si (Q₃₁)(Q₃₂)(Q₃₃) at least one of phenylene, sub- pentalene base, sub-indenyl, naphthylene, sub- camomile ring group, Asia Indacene base, sub- acenaphthenyl, fluorenylidene, the fluorenyl of sub- spiral shell two, sub- spiral shell benzfluorene-fluorenyl, sub- benzo fluorenyl, sub- dibenzo fluorenyl, Asia That non-alkenyl, phenanthrylene, anthrylene, sub- fluoranthene base, sub- benzo [9,10] phenanthryl, sub- pyrenyl, AsiaBase, subunit, Asia and five Phenyl, sub- pyrrole radicals, sub- thienyl, furylidene, sub- thiophene cough up base, sub- imidazole radicals, sub- pyrazolyl, sub- thiazolyl, sub- isothiazole Base, Ya oxazolyls, Ya isoxazolyls, sub- pyridine radicals, sub- pyrazinyl, sub- pyrimidine radicals, sub- pyridazinyl, sub- indyl, sub- iso-indoles Base, sub- indazolyl, sub- purine radicals, sub- quinolyl, sub- isoquinolyl, sub- benzoquinoline base, sub- benzisoquinoline base, sub- phthalazines Base, sub- naphthyridines base, sub- quinoxalinyl, sub- quinazolyl, sub- cinnolines base, sub- phenanthridinyl, sub- acridinyl, sub- phenanthroline, sub- fen Piperazine base, sub- benzimidazolyl, sub- benzofuranyl, sub- benzothienyl, sub- benzo thiophene cough up base, sub- benzothiazolyl, sub- different benzene Benzothiazolyl, sub- benzoxazolyl, sub- Yi benzoxazolyls, sub- triazolyl, sub- tetrazole radical, Ya oxadiazolyls, sub- triazine radical, Asia Carbazyl, sub- dibenzofuran group, sub- dibenzothiophenes base, sub- dibenzo thiophene cough up base, sub- benzo carbazole base, sub- naphtho- benzo furan Mutter base, sub- naphtho- benzothienyl, sub- naphtho- benzo thiophene coughs up base, sub- dibenzo-carbazole base, sub- dinaphtho furyl, sub- dinaphtho Thienyl, sub- dinaphtho thiophene cough up base, sub- thiadiazolyl group, sub- imidazopyridyl, sub- imidazopyrimidine base, Ya oxazoles and pyridine Base, sub- thiazolopyridinyl, sub- benzo naphthyridines base, sub- azepine fluorenyl, the fluorenyl of sub- azaspiro two, sub- azepine carbazyl, sub- azepine Dibenzofuran group, sub- azepine dibenzothiophenes base, sub- azepine dibenzo thiophene cough up base, sub- indeno-pyrrole base, sub- indoles and pyrroles Base, sub- indeno carbazyl and sub- indolocarbazole base；And

*-P (=O) (Q₄)-* ', *-P (=S) (Q₄)-* ', *-S (=O)-* ' and *-S (=O)₂- * ',

But embodiment not limited to this,

Wherein, Q₄And Q₃₁To Q₃₃Can independently selected from：

But embodiment not limited to this.

In one or more embodiments, the L in formula 2₁₁*-P (=O) (Q can be selected from₄)-* ', *-P (=S) (Q₄)-* ', *-S (=O)-* ', *-S (=O)₂- * ' and the group represented by formula 3-1 to formula 3-47, but embodiment is not limited to This：

Wherein, in formula 3-1 into formula 3-47,

Y₁Can be O, S, C (Z₃)(Z₄)、N(Z₅) or Si (Z₆)(Z₇),

Z₁To Z₇Can independently selected from：

Hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkyl, C₁-C₂₀Alcoxyl Base, cyclopenta, cyclohexyl, suberyl, cyclopentenyl, cyclohexenyl group, phenyl, xenyl, terphenyl, pentalene base, Indenyl, naphthyl, camomile ring group, indacene base, acenaphthenyl, fluorenyl, the fluorenyl of spiral shell two, spiral shell benzfluorene-fluorenyl, benzo fluorenyl, dibenzo Fluorenyl, that non-alkenyl, phenanthryl, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, base, pentacene base, pyrroles Base, thienyl, furyl, thiophene cough up base, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyls, pyridine radicals, Pyrazinyl, pyrimidine radicals, pyridazinyl, indyl, isoindolyl, indazolyl, purine radicals, quinolyl, isoquinolyl, benzoquinoline Base, isoquinolyl, phthalazinyl, naphthyridines base, quinoxalinyl, Benzoquinoxalines base, quinazolyl, Benzoquinazole base, cinnolines base, Phenanthridinyl, acridinyl, phenanthroline, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzo thiophene cough up base, benzene Benzothiazolyl, different benzothiazolyl, benzoxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, oxadiazolyls, triazine radical, Carbazyl, dibenzofuran group, dibenzothiophenes base, dibenzo thiophene cough up base, benzo carbazole base, naphtho- benzofuranyl, naphtho- Benzothienyl, naphtho- benzo thiophene are coughed up base, dibenzo-carbazole base, dinaphtho furyl, dinaphtho thienyl, dinaphtho thiophene and coughed up Base, thiadiazolyl group, imidazopyridyl, imidazopyrimidine base, oxazoles and pyridine radicals, thiazolopyridinyl, benzo naphthyridines base, nitrogen Miscellaneous fluorenyl, the fluorenyl of azaspiro two, azepine carbazyl, azepine dibenzofuran group, azepine dibenzothiophenes base, azepine dibenzo thiophene Cough up base, indeno-pyrrole base, indoles and pyrrole radicals, indeno carbazyl and indolocarbazole base, but embodiment not limited to this,

Q₄Hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C can be selected from₁-C₆₀Alkane Base, phenyl, xenyl and terphenyl；And

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group and C₁-C₆₀Alkane Phenyl, xenyl and the terphenyl of at least one of base,

D2 can be selected from 1 and 2 integer,

D3 can be selected from 1 to 3 integer,

D4 can be selected from 1 to 4 integer,

D5 can be selected from 1 to 5 integer,

D6 can be selected from 1 to 6 integer, and

D8 can be selected from 1 to 8 integer.

In one or more embodiments, the L in formula 2₁₁*-P (=O) (Q can be selected from₄)-* ' and by formula 3-1, The group that formula 3-2, formula 3-3, formula 3-6, formula 3-12, formula 3-14, formula 3-31 and formula 3-47 are represented, but embodiment not limited to this, Q₄Hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C can be selected from₁-C₆₀Alkyl, phenyl, Xenyl and terphenyl；And substitution have selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, Hydrazone group and C₁-C₆₀Phenyl, xenyl and the terphenyl of at least one of alkyl.

In one or more embodiments, the L in formula 2₁₁The group represented by formula 4-1 to formula 4-30 can be selected from, But embodiment not limited to this：

A11 in formula 2 can be but the embodiment not limited to this selected from 0 to 3 integer.In one or more realities Apply in example, a11 can be 0,1 or 2, but embodiment not limited to this.For example, a11 can be 0 or 1.When a11 is two or bigger When, two or more L₁₁Can be with mutually the same or different from each other.When a11 is zero, L₁₁It can be singly-bound.

R in formula 2₁₂Substituted or unsubstituted C can be selected from₃-C₁₀Cycloalkyl, substituted or unsubstituted C₁-C₁₀Heterocycle Alkyl, substituted or unsubstituted C₃-C₁₀Cycloalkenyl group, substituted or unsubstituted C₁-C₁₀Heterocycloalkenyl, substituted or unsubstituted C₆- C₆₀Aryl, substituted or unsubstituted C₆-C₆₀Aryloxy group, substituted or unsubstituted C₆-C₆₀Arylthio, substituted or unsubstituted C₁- C₆₀Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensation polycyclic base, the condensation of substituted or unsubstituted monovalent non-aromatic are miscellaneous more Ring group ,-Si (Q₄)(Q₅)(Q₆)、-N(Q₄)(Q₅)、-B(Q₄)(Q₅) ,-C (=O) (Q₄) ,-P (=O) (Q₄)(Q₅) ,-P (=S) (Q₄)(Q₅) ,-S (=O) (Q₄) and-S (=O)₂(Q₄), but embodiment not limited to this.

In one or more embodiments, the R in formula 2₁₂It can be selected from：

Phenyl, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthracene Base, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, base, pentaphene base, hexacene base, pentacene base, thienyl, furans Base, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzene And carbazyl, dibenzo-carbazole base, dibenzo thiophene cough up base, pyridine radicals, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazoles Base, isoxazolyls, thiadiazolyl group, oxadiazolyls, pyrazinyl, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinolyl, benzene And quinolyl, phthalazinyl, naphthyridines base, quinoxalinyl, quinazolyl, cinnolines base, phenanthridinyl, acridinyl, benzacridine base, phenanthrene are coughed up Quinoline base, phenazinyl, benzimidazolyl, different benzothiazolyl, benzoxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, miaow Azoles and pyridine radicals, imidazopyrimidine base and azepine carbazyl；And

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkane Base, C₁-C₂₀Alkoxy, phenyl, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, phenanthrene Base, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, base, pentaphene base, hexacene base, pentacene base, thiophene Base, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzo thiophene Fen base, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene cough up base, pyridine radicals, imidazole radicals, pyrazolyl, thiazolyl, isothiazole Ji, oxazolyl, isoxazolyls, thiadiazolyl group, oxadiazolyls, pyrazinyl, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinoline Quinoline base, benzoquinoline base, phthalazinyl, naphthyridines base, quinoxalinyl, quinazolyl, cinnolines base, phenanthridinyl, acridinyl, benzacridine Base, phenanthroline, phenazinyl, benzimidazolyl, different benzothiazolyl, benzoxazolyl, Yi benzoxazolyls, triazolyl, four The phenyl of at least one of oxazolyl, imidazopyridyl, imidazopyrimidine base and azepine carbazyl, xenyl, terphenyl, Naphthyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, base, pentaphene base, hexacene base, pentacene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzo Furyl, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene Cough up base, pyridine radicals, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyls, thiadiazolyl group, oxadiazolyls, Pyrazinyl, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinolyl, benzoquinoline base, phthalazinyl, naphthyridines base, quinoxaline Base, quinazolyl, cinnolines base, phenanthridinyl, acridinyl, benzacridine base, phenanthroline, phenazinyl, benzimidazolyl, different benzo Thiazolyl, benzoxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, imidazopyridyl, imidazopyrimidine base and azepine Carbazyl；And

-B(Q₄)(Q₅) ,-P (=O) (Q₄)(Q₅) ,-P (=S) (Q₄)(Q₅) ,-S (=O) (Q₄) and-S (=O)₂(Q₄), but It is embodiment not limited to this,

Wherein, Q₄、Q₅And Q₆Can independently selected from：

But embodiment not limited to this.

In one or more embodiments, the R in formula 2₁₂- B (Q can be selected from₄)(Q₅) ,-P (=O) (Q₄)(Q₅)、- P (=S) (Q₄)(Q₅) ,-S (=O) (Q₄) ,-S (=O)₂(Q₄) and the group that is represented by formula 5-1 to formula 5-90, but embodiment is not It is limited to this：

Wherein, in formula 5-1 into formula 5-90,

Y₃₁Can be O, S, C (Z₃₄)(Z₃₅)、N(Z₃₆) or Si (Z₃₇)(Z₃₈),

Z₃₁To Z₃₈Can independently selected from：

Q₄And Q₅Can be independently selected from C₁-C₁₀Alkyl, C₁-C₁₀Alkoxy, phenyl, xenyl, terphenyl, naphthalene Base, pyridine radicals, pyrimidine radicals, pyrazinyl, quinolyl, isoquinolyl, quinoxalinyl and quinazolyl；And

E2 can be selected from 1 and 2 integer,

E3 can be selected from 1 to 3 integer,

E4 can be selected from 1 to 4 integer,

E5 can be selected from 1 to 5 integer,

E6 can be selected from 1 to 6 integer,

E7 can be selected from 1 to 7 integer, and

E9 can be selected from 1 to 9 integer.

In one or more embodiments, R₁₂- B (Q can be selected from₄)(Q₅) ,-P (=O) (Q₄)(Q₅) and by formula The group that 5-1, formula 5-3, formula 5-4, formula 5-13 to formula 5-15 and formula 5-21 represent to formula 5-23, but embodiment not limited to this； And

Q₄And Q₅Can independently selected from hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, Hydrazone group, C₁-C₆₀Alkyl, phenyl, xenyl and terphenyl；And

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group and C₁-C₆₀Alkane Phenyl, xenyl and the terphenyl of at least one of base.

In one or more embodiments, the R in formula 2₁₂The group represented by formula 6-1 to formula 6-22 can be selected from, But embodiment not limited to this：

B12 in formula 2 can be but the embodiment not limited to this selected from 1 to 3 integer.For example, b12 can be 1 or 2.When b12 is two or bigger, two or more R₁₂Can be with mutually the same or different from each other.

In one or more embodiments, in formula 1,

R₁To R₄And R₆To R₁₁Can independently selected from：

Substitution has in deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl and hydrazone group at least The C of one₁-C₂₀Alkyl and C₁-C₂₀Alkoxy；And

-Si(Q₁)(Q₂)(Q₃),

R₅Can be the group represented by formula 2,

In formula 2,

L₁₁The group represented by formula 4-1 to formula 4-30 can be selected from,

A11 can be selected from 0 to 2 integer,

R₁₂The group represented by formula 6-1 to formula 6-22 can be selected from,

B12 can be 1 or 2,

Q₁To Q₃Can be independently selected from C₁-C₂₀Alkyl, C₁-C₂₀Alkoxy, phenyl and naphthyl：

The heterocyclic compound represented by formula 1 can be the one kind selected from following compound 1 into compound 87, still Embodiment not limited to this：

The heterocyclic compound represented by formula 1 can include benzacridine core.The heterocyclic compound can be in total It is middle to form pi-conjugated system, and can have the low structure of intramolecular steric hindrance.Therefore, can be advantageous to tight between molecule Closs packing, so as to improve charge transport ability.In addition, the pi-conjugated structure of the heterocyclic compound can be to high glass transition temperature Degree (Tg) and high-melting-point contribute.Therefore, including the organic luminescent device of the heterocyclic compound can have high-durability, with And such as low driving voltage and efficient excellent device property in operation.

In the exemplary embodiment, there is the heterocyclic compound substituent benzacridine core is connected at C5 carbon locations Structure.The heterocyclic compound can have the intramolecular steric hindrance reduced between connecting portion and substituent, and can have There is the less dihedral angle of expansible pi-conjugated system.In addition, molecule can have rod-shape, the heterocyclic compound as overall There can be higher electron mobility.

It is pi-conjugated can due to steric hindrance and by anthracene core 9,10 substitution bending failures.However, 2,6 substitutions can subtract Small dihedral angle simultaneously extends pi-conjugated system, and it can provide the effect of high electron mobility.

The synthetic method of the heterocyclic compound represented with reference to Examples provided below description by formula 1.

At least one of heterocyclic compound represented by formula 1 can make between a pair of electrodes of organic luminescent device With.For example, the heterocyclic compound can be included at least one in electron transporting zone and emission layer.In another embodiment party In formula, the heterocyclic compound represented by formula 1 may be used as being arranged on outside the pair of electrode of organic luminescent device for being formed The material of the coating of side.

According to one or more embodiments, organic luminescent device can include：First electrode；Second electrode, in face of One electrode；And organic layer, be arranged between first electrode and second electrode, and including emission layer, wherein, organic layer include by At least one of heterocyclic compound that formula 1 represents.

Statement " (organic layer) includes at least one of heterocyclic compound " used herein can include " (organic layer) bag Include the identical heterocyclic compound represented by formula 1 " situation and " (organic layer) include represented by formula 1 two or more The situation of different heterocyclic compound ".

For example, organic layer can only include the compound 1 as heterocyclic compound.On this point, compound 1 can deposit In the electron transfer layer in organic luminescent device.In one or more embodiments, organic layer can include being used as heterocycle The compound 1 and compound 2 of compound.On this point, compound 1 and compound 2 may reside in same layer (for example, Compound 1 and compound 2 all can be present in emission layer) or different layers in (for example, compound 1 may reside in electronics In transport layer, compound 2 may reside in emission layer；Or compound 1 may reside in emission layer, compound 2 can be with It is present in electron transfer layer).

In the exemplary embodiment, organic layer includes：I) hole transporting zone, first electrode (anode) and emission layer are arranged on Between, and including at least one in hole injection layer, hole transmission layer, cushion and electronic barrier layer；And ii) electronics biography Defeated region, it is arranged between emission layer and second electrode (negative electrode), and including hole blocking layer, electron transfer layer and electron injection It is at least one in layer.At least one heterocycle that can include being represented by formula 1 selected from electron transporting zone and emission layer At least one of compound.For example, electron transporting zone can include electron injecting layer and electron transfer layer, from electron injection What is selected in layer and electron transfer layer at least one can include at least one of described heterocyclic compound.In one embodiment In, electron transporting zone can include electron transfer layer, wherein, electron transfer layer can be included in the heterocyclic compound extremely Few one kind.In one embodiment, emission layer can include pyrene compound, but embodiment not limited to this.

Organic luminescent device can also be at least one including being selected from the first coating and the second coating, and the first coating is set Put on the path that caused light is advanced through first electrode towards outside in emission layer, the second coating, which is arranged in emission layer, to be produced Raw light through second electrode towards the outside path advanced on, selected from the first coating and the second coating described at least one It is individual to include at least one of described heterocyclic compound.

For example, organic luminescent device can have：I) stacked structure, it includes what is stacked with the order of order of the statement First electrode, organic layer, second electrode and the second coating；Ii) stacked structure, it includes stacking with the order of order of the statement The first coating, first electrode, organic layer and second electrode；Or iii) stacked structure, it includes suitable with the order of the statement The first coating, first electrode, organic layer, second electrode and the second coating stacked to sequence, from the first coating and the second coating At least one of selection can include the heterocyclic compound.

Term " organic layer " as used herein refers to the individual layer between the first electrode of organic luminescent device and second electrode And/or multiple layers.The material being included in " organic layer " is not limited to organic material.

Fig. 1 is the schematic diagram according to the organic luminescent device 10 of embodiment.Organic luminescent device 10 is included with the statement First electrode 110, organic layer 150 and the second electrode 190 stacked to order of order.

Hereinafter, structure and manufacture organic light emission of Fig. 1 descriptions according to the organic luminescent device 10 of embodiment will be combined The method of device 10.

In Fig. 1, substrate can be arranged on the lower section of first electrode 110 or the top of second electrode 190.Substrate can be for example Substrate of glass or plastic-substrates, it is every kind of with excellent mechanical strength, heat endurance, transparency, surfacing in them Degree, tractability and water proofing property.

For example, the first electricity can be formed by depositing or sputtering in substrate for forming the material of first electrode 110 Pole 110.When first electrode 110 is anode, the material for forming first electrode 110 can be selected from for example to be escaped with height The material of work(, to promote hole to inject.

First electrode 110 can be such as reflecting electrode, half transmitting electrode or transmission electrode.When first electrode 110 is During radio pole, for formed first electrode 110 material can be selected from for example tin indium oxide (ITO), indium zinc oxide (IZO), Tin oxide (SnO₂), zinc oxide (ZnO) and their any combination, but embodiment not limited to this.When first electrode 110 is half When transmission electrode or reflecting electrode, as the material for forming first electrode 110, such as can use magnesium (Mg), silver-colored (Ag), Aluminium (Al), aluminium-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) or their any combination.However, with In the material not limited to this for forming first electrode 110.

First electrode 110 can have single layer structure or the sandwich construction including two or more layers.For example, first Electrode 110 can have ITO/Ag/ITO three-decker, but the structure not limited to this of first electrode 110.

Organic layer 150 can be arranged in first electrode 110.Organic layer 150 can include emission layer.

Organic layer 150 can also include hole transporting zone for example between first electrode 110 and emission layer and Electron transporting zone between emission layer and second electrode 190.

Hole transporting zone can have for example：I) single layer structure, it includes the individual layer comprising single material；Ii) individual layer Structure, it includes the individual layer for including a variety of different materials；Or iii) sandwich construction, its have include the more of a variety of different materials Individual layer.

Hole transporting zone can be included for example from hole injection layer, hole transmission layer, transmitting auxiliary layer and electronic blocking At least one layer selected in layer.For example, hole transporting zone can have：Including the individual layer comprising a variety of different materials Single layer structure, or with hole injection layer/hole transport Rotating fields, hole injection layer/hole transmission layer/transmitting auxiliary layer knot Structure, hole injection layer/transmitting auxiliary Rotating fields, hole transmission layer/transmitting auxiliary Rotating fields or hole injection layer/hole transport The sandwich construction of layer/electron barrier layer structure, wherein, for every kind of structure, with the order of the statement from the order of first electrode 110 Ground, which stacks, forms layer, but the structure not limited to this of hole transporting zone.

Hole transporting zone can include for example from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, Spiral shell-TPD, spiral shell-NPB, methylate NPB, TAPC, HMTPD, 4,4', 4 "-three (N- carbazyls) triphenylamines (TCTA), polyaniline/ten Dialkyl benzene sulfonic acids (PANI/DBSA), PEDOT/PSS (poly- (3,4- ethylenedioxy thiophenes)/poly- (4- styrene sulfonates)), gather Aniline/camphorsulfonic acid (PANI/CSA), polyaniline/poly- (4- styrene sulfonates) (PANI/PSS), the chemical combination represented by formula 201 At least one selected in thing and the compound represented by formula 202：

And

In formula 201 and formula 202,

L₂₀₁To L₂₀₄Can be independently selected from substituted or unsubstituted C₃-C₁₀It is cycloalkylidene, substituted or unsubstituted C₁-C₁₀Sub- Heterocyclylalkyl, substituted or unsubstituted C₃-C₁₀Sub- cycloalkenyl group, substituted or unsubstituted C₁-C₁₀Sub- heterocycloalkenyl, take Generation or unsubstituted C₆-C₆₀Arlydene, substituted or unsubstituted C₁-C₆₀Inferior heteroaryl, substituted or unsubstituted divalence are non-aromatic Condensation polycyclic base and the non-aromatic miscellaneous more ring groups of condensation of substituted or unsubstituted divalence,

L₂₀₅*-O-*', *-S-*', *-N (Q can be selected from₂₀₁)-* ', substituted or unsubstituted C₁-C₂₀Alkylidene, substitution Or unsubstituted C₂-C₂₀Alkenylene, substituted or unsubstituted C₃-C₁₀Cycloalkylidene, substituted or unsubstituted C₁-C₁₀Sub- heterocycle alkane Base, substituted or unsubstituted C₃-C₁₀Sub- cycloalkenyl group, substituted or unsubstituted C₁-C₁₀It is sub- heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Arlydene, substituted or unsubstituted C₁-C₆₀The non-aromatic condensation polycyclic base of inferior heteroaryl, substituted or unsubstituted divalence and The substituted or unsubstituted non-aromatic miscellaneous more ring groups of condensation of divalence,

Xa1 to xa4 can independently be selected from 0 to 3 integer,

Xa5 can be selected from 1 to 10 integer,

R₂₀₁To R₂₀₄And Q₂₀₁Can be independently selected from substituted or unsubstituted C₃-C₁₀Cycloalkyl, substitution or unsubstituted C₁-C₁₀Heterocyclylalkyl, substituted or unsubstituted C₃-C₁₀Cycloalkenyl group, substituted or unsubstituted C₁-C₁₀Heterocycloalkenyl, substitution or Unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₆-C₆₀Aryloxy group, substituted or unsubstituted C₆-C₆₀Arylthio, substitution or Unsubstituted C₁-C₆₀Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensation polycyclic base and substituted or unsubstituted unit price are non- Fragrance is condensed miscellaneous more ring groups.

For example, the R in formula 202₂₀₁And R₂₀₂Can be selectively via singly-bound, dimethyl-methylene or diphenyl-methylene Base connects, R₂₀₃And R₂₀₄Selectively it can be connected via singly-bound, dimethyl-methylene or diphenyl-methylene.

In one or more embodiments, in formula 201 and formula 202,

L₂₀₁To L₂₀₅Can independently selected from：

Phenylene, sub- pentalene base, sub-indenyl, naphthylene, sub- camomile ring group, sub- heptalene base, sub- indacene base, Sub- acenaphthenyl, fluorenylidene, the fluorenyl of sub- spiral shell two, sub- benzo fluorenyl, sub- dibenzo fluorenyl, that alkenyl of Asia and Africa, phenanthrylene, anthrylene, Asia Fluoranthene base, sub- benzo [9,10] phenanthryl, sub- pyrenyl, AsiaBase, sub- aphthacene base, Ya Pi base, subunit, sub- pentaphene base, Asia are simultaneously Hexaphenyl, sub- pentacene base, sub- rubicene base, Ya guans base, sub- ovalene base, sub- thienyl, furylidene, sub- carbazyl, sub- Yin Diindyl base, sub- isoindolyl, sub- benzofuranyl, sub- benzothienyl, sub- dibenzofuran group, sub- dibenzothiophenes base, sub- benzene And carbazyl, sub- dibenzo-carbazole base, sub- dibenzo thiophene cough up base and sub- pyridine radicals；And

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkane Base, C₁-C₂₀Alkoxy, cyclopenta, cyclohexyl, suberyl, cyclopentenyl, cyclohexenyl group, phenyl, xenyl, terphenyl, take , there is C in generation₁-C₁₀The phenyl of alkyl, substitution have-F phenyl, pentalene base, indenyl, naphthyl, camomile ring group, heptalene base, Indacene base, acenaphthenyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, that non-alkenyl, phenanthryl, anthryl, fluoranthene base, benzene And [9,10] phenanthryl, pyrenyl,Base, aphthacene Ji, Pi base, base, pentaphene base, hexacene base, pentacene base, rubicene base, Guan base, ovalene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzo Furyl, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene cough up base, pyridine radicals ,-Si (Q₃₁)(Q₃₂) (Q₃₃) and-N (Q₃₁)(Q₃₂) at least one of phenylene, sub- pentalene base, sub-indenyl, naphthylene, sub- azulenes Base, sub- heptalene base, sub- indacene base, sub- acenaphthenyl, fluorenylidene, the fluorenyl of sub- spiral shell two, sub- benzo fluorenyl, sub- dibenzo fluorenyl, Asia That non-alkenyl, phenanthrylene, anthrylene, sub- fluoranthene base, sub- benzo [9,10] phenanthryl, sub- pyrenyl, AsiaBase, sub- aphthacene base, Asia Pi base, subunit, sub- pentaphene base, sub- hexacene base, sub- pentacene base, sub- rubicene base, Ya guans base, sub- ovalene base, sub- thiophene Base, furylidene, sub- carbazyl, sub- indyl, sub- isoindolyl, sub- benzofuranyl, sub- benzothienyl, sub- dibenzo furan Mutter base, sub- dibenzothiophenes base, sub- benzo carbazole base, sub- dibenzo-carbazole base, sub- dibenzo thiophene coughs up base and sub- pyridine radicals,

Wherein, Q₃₁To Q₃₃Can be independently selected from C₁-C₁₀Alkyl, C₁-C₁₀Alkoxy, phenyl, xenyl, three Phenyl and naphthyl.

In one or more embodiments, xa1 to xa4 can independently be 0,1 or 2.

In one or more embodiments, xa5 can be 1,2,3 or 4.

In one or more embodiments, R₂₀₁To R₂₀₄And Q₂₀₁Can be independently selected from phenyl, xenyl, three Xenyl, pentalene base, indenyl, naphthyl, camomile ring group, heptalene base, indacene base, acenaphthenyl, fluorenyl, the fluorenyl of spiral shell two, Benzo fluorenyl, dibenzo fluorenyl, that non-alkenyl, phenanthryl, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base and four Phenyl, Pi base, base, pentaphene base, hexacene base, pentacene base, rubicene Ji, guans base, ovalene base, thienyl, furyl, click Oxazolyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole Base, dibenzo-carbazole base, dibenzo thiophene cough up base and pyridine radicals；And

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkane Base, C₁-C₂₀Alkoxy, cyclopenta, cyclohexyl, suberyl, cyclopentenyl, cyclohexenyl group, phenyl, xenyl, terphenyl, take , there is C in generation₁-C₁₀The phenyl of alkyl, substitution have-F phenyl, pentalene base, indenyl, naphthyl, camomile ring group, heptalene base, Indacene base, acenaphthenyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, that non-alkenyl, phenanthryl, anthryl, fluoranthene base, benzene And [9,10] phenanthryl, pyrenyl,Base, aphthacene Ji, Pi base, base, pentaphene base, hexacene base, pentacene base, rubicene base, Guan base, ovalene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzo Furyl, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene cough up base, pyridine radicals ,-Si (Q₃₁)(Q₃₂) (Q₃₃) and-N (Q₃₁)(Q₃₂) at least one of phenyl, xenyl, terphenyl, pentalene base, indenyl, naphthyl, sweet Chrysanthemum ring group, heptalene base, indacene base, acenaphthenyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, that non-alkenyl, phenanthrene Base, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, aphthacene Ji, Pi base, base, pentaphene base, hexacene base, Pentacene base, rubicene Ji, guans base, ovalene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzofuran Base, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene cough up base And pyridine radicals,

Wherein, Q₃₁To Q₃₃With same as described above.

In one or more embodiments, the R from formula 201₂₀₁To R₂₀₃At least one of middle selection can be independent Ground is selected from：

Fluorenyl, the fluorenyl of spiral shell two, carbazyl, dibenzofuran group and dibenzothiophenes base；And

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkane Base, C₁-C₂₀Alkoxy, cyclopenta, cyclohexyl, suberyl, cyclopentenyl, cyclohexenyl group, phenyl, xenyl, terphenyl, take , there is C in generation₁-C₁₀The phenyl of alkyl, substitution have-F phenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell two, carbazyl, dibenzofuran group and two Fluorenyl, the fluorenyl of spiral shell two, carbazyl, dibenzofuran group and the dibenzothiophenes base of at least one of benzothienyl；

But embodiment not limited to this.

In one or more embodiments, in formula 202, i) R₂₀₁And R₂₀₂It can be connected via singly-bound, and/or ii)R₂₀₃And R₂₀₄It can be connected via singly-bound.

In one or more embodiments, the R from formula 202₂₀₁To R₂₀₄At least one of middle selection can be selected from：

Carbazyl；And

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkyl, C₁-C₂₀Alkoxy, cyclopenta, cyclohexyl, suberyl, cyclopentenyl, cyclohexenyl group, phenyl, xenyl, terphenyl, substitution There is C₁-C₁₀The phenyl of alkyl, substitution have-F phenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell two, carbazyl, dibenzofuran group and hexichol The carbazyl of at least one of bithiophene base；

But embodiment not limited to this.

The compound represented by formula 201 can be represented by formula 201A：

In one embodiment, the compound represented by formula 201 can be represented by following formula 201A (1), but be implemented Example not limited to this：

In one embodiment, the compound represented by formula 201 can be represented by following formula 201A-1, but embodiment Not limited to this：

In one embodiment, the compound represented by formula 202 can be represented by formula 202A：

In one embodiment, the compound represented by formula 202 can be represented by formula 202A-1：

In formula 201A, formula 201A (1), formula 201A-1, formula 202A and formula 202A-1,

L₂₀₁To L₂₀₃, xa1 to xa3, xa5 and R₂₀₂To R₂₀₄Can with same as described above,

R₂₁₁And R₂₁₂Can with reference to R₂₀₃What is described is identical.

R₂₁₃To R₂₁₇Can be independently selected from hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, hydrazine Base, hydrazone group, C₁-C₂₀Alkyl, C₁-C₂₀Alkoxy, cyclopenta, cyclohexyl, suberyl, cyclopentenyl, cyclohexenyl group, phenyl, connection Phenyl, terphenyl, substitution have C₁-C₁₀The phenyl of alkyl, substitution have-F phenyl, pentalene base, indenyl, naphthyl, sweet Chrysanthemum ring group, heptalene base, indacene base, acenaphthenyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, that non-alkenyl, phenanthrene Base, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, aphthacene Ji, Pi base, base, pentaphene base, hexacene base, Pentacene base, rubicene Ji, guans base, ovalene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzofuran Base, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene cough up base And pyridine radicals.

Hole transporting zone can include at least one chemical combination for example selected from compound HT1 into compound HT39 Thing, but embodiment not limited to this：

The thickness of hole transporting zone can be for example aboutTo aboutIn the range of, for example, big AboutTo aboutIn the range of.When hole transporting zone is included in hole injection layer and hole transmission layer at least At one, the thickness of hole injection layer can be for example aboutTo aboutIn the range of, for example, aboutTo aboutIn the range of, the thickness of hole transmission layer can be for example aboutTo about's In the range of, for example, aboutTo aboutIn the range of.When hole transporting zone, hole injection layer and hole pass When the thickness of defeated layer is in the range of these, gratifying hole transporting properties can be obtained without significantly increasing driving voltage.

Transmitting auxiliary layer can compensate optical resonance distance to improve by the wavelength according to the light launched by emission layer Luminous efficiency, electronic barrier layer can stop the flowing of the electronics from electron transporting zone.Launch auxiliary layer and electronic blocking Layer can include material as described above.

In addition to these materials, the electric charge that hole transporting zone can also include being used to improve conduction property produces material Material.Charge generating material uniformly or non-uniformly can be dispersed in hole transporting zone.

Charge generating material can be such as p dopants.

In one embodiment, lowest unoccupied molecular orbital (LUMO) energy level of p dopants can be -3.5eV or smaller.

P dopants can include at least one selected from the compound of quinone derivative, metal oxide and cyano-containing, But embodiment not limited to this.

For example, p dopants can include at least one of following compound：

Quinone derivative, such as four cyano quinone bismethane (TCNQ) and 2,3,5,6- tetra- fluoro- 7,7,8,8- four cyano quinone diformazans Alkane (F4-TCNQ)；

Metal oxide, such as tungsten oxide or molybdenum oxide；

The nitrile (HAT-CN) of six azepine benzophenanthrenes of 1,4,5,8,9,12--six；And

The compound represented by following formula 221：

But embodiment not limited to this：

In formula 221,

R₂₂₁To R₂₂₃Can be independently selected from substituted or unsubstituted C₃-C₁₀Cycloalkyl, substituted or unsubstituted C₁- C₁₀Heterocyclylalkyl, substituted or unsubstituted C₃-C₁₀Cycloalkenyl group, substituted or unsubstituted C₁-C₁₀Heterocycloalkenyl, substitution or unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₁-C₆₀Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensation polycyclic base and take Generation or unsubstituted monovalent non-aromatic are condensed miscellaneous more ring groups, and precondition is from R₂₂₁To R₂₂₃Middle selection it is at least one have from Cyano group ,-F ,-Cl ,-Br ,-I, substitution have-F C₁-C₂₀Alkyl, substitution have-Cl C₁-C₂₀Alkyl, substitution have-Br C₁-C₂₀ Alkyl and substitution have-I C₁-C₂₀At least one substituent is selected in alkyl.

When organic luminescent device 10 is full-color organic light emitting device, exemplified by emission layer can be patterned according to sub-pixel Such as red emitting layers, green emission layer or blue color-emitting layers.In one or more embodiments, emission layer can have for example The stacked structure of two or more layers selected from red emitting layers, green emission layer and blue color-emitting layers, wherein, it is described Two or more layers are in contact with each other or separated each other.In one or more embodiments, emission layer can be included for example Two or more materials selected from red illuminating material, green luminescent material and blue emitting material, wherein, described two Kind or more kind material is mixed with each other in individual layer to launch white light.

Emission layer can include main body and dopant.Dopant can include for example from phosphorescent dopants and fluorescent dopants At least one of middle selection.

Based on the main body of 100 parts by weight, the amount of the dopant in emission layer generally can be in such as about 0.01 parts by weight To about 15 parts by weight, but embodiment not limited to this.

The thickness of emission layer can be for example aboutTo aboutIn the range of, for example, aboutTo aboutIn the range of.When emission layer thickness within the range when, the excellent characteristics of luminescence can be obtained and Do not significantly increase driving voltage.

In one or more embodiments, main body can include the compound for example represented by following formula 301.

[Ar₃₀₁]_xb11-[(L₃₀₁)_xb1-R₃₀₁]_xb21。

In formula 301,

Ar₃₀₁Can be substituted or unsubstituted C₅-C₆₀Carbocylic radical or substituted or unsubstituted C₁-C₆₀Heterocyclic radical,

Xb11 is 1,2 or 3；

L₃₀₁Substituted or unsubstituted C can be selected from₃-C₁₀Cycloalkylidene, substituted or unsubstituted C₁-C₁₀Sub- heterocycle alkane Base, substituted or unsubstituted C₃-C₁₀Sub- cycloalkenyl group, substituted or unsubstituted C₁-C₁₀It is sub- heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Arlydene, substituted or unsubstituted C₁-C₆₀The non-aromatic condensation polycyclic base of inferior heteroaryl, substituted or unsubstituted divalence and The substituted or unsubstituted non-aromatic miscellaneous more ring groups of condensation of divalence；

Xb1 can be selected from 0 to 5 integer,

R₃₀₁Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, substitution or not can be selected from Substituted C₁-C₆₀Alkyl, substituted or unsubstituted C₂-C₆₀Alkenyl, substituted or unsubstituted C₂-C₆₀Alkynyl, substitution or unsubstituted C₁-C₆₀Alkoxy, substituted or unsubstituted C₃-C₁₀Cycloalkyl, substituted or unsubstituted C₁-C₁₀Heterocyclylalkyl, substitution or not Substituted C₃-C₁₀Cycloalkenyl group, substituted or unsubstituted C₁-C₁₀Heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Aryl, substitution or Unsubstituted C₆-C₆₀Aryloxy group, substituted or unsubstituted C₆-C₆₀Arylthio, substituted or unsubstituted C₁-C₆₀Heteroaryl, substitution Or unsubstituted monovalent non-aromatic condensation polycyclic base, substituted or unsubstituted monovalent non-aromatic are condensed miscellaneous more ring groups ,-Si (Q₃₀₁) (Q₃₀₂)(Q₃₀₃)、-N(Q₃₀₁)(Q₃₀₂)、-B(Q₃₀₁)(Q₃₀₂) ,-C (=O) (Q₃₀₁) ,-S (=O)₂(Q₃₀₁) and-P (=O) (Q₃₀₁) (Q₃₀₂),

Xb21 can be selected from 1 to 5 integer,

Q₃₀₁To Q₃₀₃Can be independently selected from C₁-C₁₀Alkyl, C₁-C₁₀Alkoxy, phenyl, xenyl, terphenyl And naphthyl, but embodiment not limited to this.

In one embodiment, the Ar in formula 301₃₀₁It can be selected from：

Naphthyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, that non-alkenyl, phenanthryl, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, aphthacene Ji, Pi base, base, pentaphene base, indeno anthryl, dibenzofuran group and dibenzo Thienyl；And

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkane Base, C₁-C₂₀Alkoxy, phenyl, xenyl, terphenyl, naphthyl ,-Si (Q₃₁)(Q₃₂)(Q₃₃)、-N(Q₃₁)(Q₃₂)、-B(Q₃₁) (Q₃₂) ,-C (=O) (Q₃₁) ,-S (=O)₂(Q₃₁) and-P (=O) (Q₃₁)(Q₃₂) at least one of naphthyl, fluorenyl, the fluorenes of spiral shell two Base, benzo fluorenyl, dibenzo fluorenyl, that non-alkenyl, phenanthryl, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, simultaneously Tetraphenyl, Pi base, base, pentaphene base, indeno anthryl, dibenzofuran group and dibenzothiophenes base,

Wherein, Q₃₁To Q₃₃Can be independently selected from C₁-C₁₀Alkyl, C₁-C₁₀Alkoxy, phenyl, xenyl, three Phenyl and naphthyl, but embodiment not limited to this.

When the xb11 in formula 301 is two or bigger, two or more Ar₃₀₁It can be connected via singly-bound.

In one or more embodiments, the compound represented by formula 301 can be represented by formula 301-1 or formula 301-2：

In formula 301-1 into formula 301-2,

A₃₀₁To A₃₀₄Can independently selected from phenyl, naphthyl, phenanthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, pyridine radicals, pyrimidine radicals, indenyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, indyl, carbazyl, benzo Carbazyl, dibenzo-carbazole base, furyl, benzofuranyl, dibenzofuran group, aphthofurans base, benzo aphthofurans base, Dinaphtho furyl, thienyl, benzothienyl, dibenzothiophenes base, aphthothiophenes base, benzo aphthothiophenes base and dinaphtho Thienyl,

X₃₀₁Can be O, S or N- [(L₃₀₄)_xb4-R₃₀₄],

R₃₁₁To R₃₁₄Can be independently selected from hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, hydrazine Base, hydrazone group, C₁-C₂₀Alkyl, C₁-C₂₀Alkoxy, phenyl, xenyl, terphenyl, naphthyl ,-Si (Q₃₁)(Q₃₂)(Q₃₃)、-N (Q₃₁)(Q₃₂)、-B(Q₃₁)(Q₃₂) ,-C (=O) (Q₃₁) ,-S (=O)₂(Q₃₁) and-P (=O) (Q₃₁)(Q₃₂),

Xb22 and xb23 can independently be 0,1 or 2,

L₃₀₁、xb1、R₃₀₁And Q₃₁To Q₃₃Can with same as described above,

L₃₀₂To L₃₀₄Can independently with reference to L₃₀₁What is described is identical,

Xb2 to xb4 can be independently identical with combination xb1 descriptions, and

R₃₀₂To R₃₀₄Can independently with reference to R₃₀₁What is described is identical.

For example, the L in formula 301, formula 301-1 and formula 301-2₃₀₁To L₃₀₄Can independently selected from：

Phenylene, naphthylene, fluorenylidene, the fluorenyl of sub- spiral shell two, sub- benzo fluorenyl, sub- dibenzo fluorenyl, phenanthrylene, sub- anthracene Base, sub- fluoranthene base, sub- benzo [9,10] phenanthryl, sub- pyrenyl, AsiaBase, subunit, sub- pentaphene base, sub- hexacene base, Asia and five Phenyl, sub- thienyl, furylidene, sub- carbazyl, sub- indyl, sub- isoindolyl, sub- benzofuranyl, sub- benzothiophene Base, sub- dibenzofuran group, sub- dibenzothiophenes base, sub- benzo carbazole base, sub- dibenzo-carbazole base, sub- dibenzo thiophene cough up base, Sub- pyridine radicals, sub- imidazole radicals, sub- pyrazolyl, sub- thiazolyl, sub- isothiazolyl, Ya oxazolyls, Ya isoxazolyls, sub- thiadiazoles Base, Ya oxadiazolyls, sub- pyrazinyl, sub- pyrimidine radicals, sub- pyridazinyl, sub- triazine radical, sub- quinolyl, sub- isoquinolyl, sub- benzo Quinolyl, sub- phthalazinyl, sub- naphthyridines base, sub- quinoxalinyl, sub- quinazolyl, sub- cinnolines base, sub- phenanthridinyl, sub- acridinyl, Asia Phenanthroline, sub- phenazinyl, sub- benzimidazolyl, sub- different benzothiazolyl, sub- benzoxazolyl, sub- Yi benzoxazolyls, Asia Triazolyl, sub- tetrazole radical, sub- imidazopyridyl, sub- imidazopyrimidine base and sub- azepine carbazyl；And

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkane Base, C₁-C₂₀Alkoxy, phenyl, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, phenanthrene Base, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, base, pentaphene base, hexacene base, pentacene base, thiophene Base, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzo thiophene Fen base, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene cough up base, pyridine radicals, imidazole radicals, pyrazolyl, thiazolyl, isothiazole Ji, oxazolyl, isoxazolyls, thiadiazolyl group, oxadiazolyls, pyrazinyl, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinoline Quinoline base, benzoquinoline base, phthalazinyl, naphthyridines base, quinoxalinyl, quinazolyl, cinnolines base, phenanthridinyl, acridinyl, phenanthroline Base, phenazinyl, benzimidazolyl, different benzothiazolyl, benzoxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, imidazoles And pyridine radicals, imidazopyrimidine base, azepine carbazyl ,-Si (Q₃₁)(Q₃₂)(Q₃₃)、-N(Q₃₁)(Q₃₂)、-B(Q₃₁)(Q₃₂)、-C (=O) (Q₃₁) ,-S (=O)₂(Q₃₁) and-P (=O) (Q₃₁)(Q₃₂) at least one of phenylene, naphthylene, fluorenylidene, Asia The fluorenyl of spiral shell two, sub- benzo fluorenyl, sub- dibenzo fluorenyl, phenanthrylene, anthrylene, sub- fluoranthene base, sub- benzo [9,10] phenanthryl, sub- pyrene Base, AsiaBase, subunit, sub- pentaphene base, sub- hexacene base, sub- pentacene base, sub- thienyl, furylidene, sub- carbazyl, Asia Indyl, sub- isoindolyl, sub- benzofuranyl, sub- benzothienyl, sub- dibenzofuran group, sub- dibenzothiophenes base, Asia Benzo carbazole base, sub- dibenzo-carbazole base, sub- dibenzo thiophene cough up base, sub- pyridine radicals, sub- imidazole radicals, sub- pyrazolyl, sub- thiazolyl, Sub- isothiazolyl, Ya oxazolyls, Ya isoxazolyls, sub- thiadiazolyl group, Ya oxadiazolyls, sub- pyrazinyl, sub- pyrimidine radicals, sub- pyridazine Base, sub- triazine radical, sub- quinolyl, sub- isoquinolyl, sub- benzoquinoline base, sub- phthalazinyl, sub- naphthyridines base, sub- quinoxalinyl, Asia Quinazolyl, sub- cinnolines base, sub- phenanthridinyl, sub- acridinyl, sub- phenanthroline, sub- phenazinyl, sub- benzimidazolyl, sub- different benzo Thiazolyl, sub- benzoxazolyl, sub- Yi benzoxazolyls, sub- triazolyl, sub- tetrazole radical, sub- imidazopyridyl, sub- imidazo Pyrimidine radicals and sub- azepine carbazyl,

Wherein, Q₃₁To Q₃₃Can be with same as described above.

In one or more embodiments, the R in formula 301, formula 301-1 and formula 301-2₃₀₁To R₃₀₄Can independently It is selected from：

Phenyl, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthracene Base, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, base, pentaphene base, hexacene base, pentacene base, thienyl, furans Base, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzene And carbazyl, dibenzo-carbazole base, dibenzo thiophene cough up base, pyridine radicals, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazoles Base, isoxazolyls, thiadiazolyl group, oxadiazolyls, pyrazinyl, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinolyl, benzene And quinolyl, phthalazinyl, naphthyridines base, quinoxalinyl, quinazolyl, cinnolines base, phenanthridinyl, acridinyl, phenanthroline, azophenlyene Base, benzimidazolyl, different benzothiazolyl, benzoxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, imidazopyridine Base, imidazopyrimidine base and azepine carbazyl；And

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkane Base, C₁-C₂₀Alkoxy, phenyl, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, phenanthrene Base, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, base, pentaphene base, hexacene base, pentacene base, thiophene Base, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzo thiophene Fen base, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene cough up base, pyridine radicals, imidazole radicals, pyrazolyl, thiazolyl, isothiazole Ji, oxazolyl, isoxazolyls, thiadiazolyl group, oxadiazolyls, pyrazinyl, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinoline Quinoline base, benzoquinoline base, phthalazinyl, naphthyridines base, quinoxalinyl, quinazolyl, cinnolines base, phenanthridinyl, acridinyl, phenanthroline Base, phenazinyl, benzimidazolyl, different benzothiazolyl, benzoxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, imidazoles And pyridine radicals, imidazopyrimidine base, azepine carbazyl ,-Si (Q₃₁)(Q₃₂)(Q₃₃)、-N(Q₃₁)(Q₃₂)、-B(Q₃₁)(Q₃₂)、-C (=O) (Q₃₁) ,-S (=O)₂(Q₃₁) and-P (=O) (Q₃₁)(Q₃₂) at least one of phenyl, xenyl, terphenyl, naphthalene Base, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl, Base, base, pentaphene base, hexacene base, pentacene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzo furan Mutter base, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene is coughed up Base, pyridine radicals, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyls, thiadiazolyl group, oxadiazolyls, pyrrole Piperazine base, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinolyl, benzoquinoline base, phthalazinyl, naphthyridines base, quinoxalinyl, Quinazolyl, cinnolines base, phenanthridinyl, acridinyl, phenanthroline, phenazinyl, benzimidazolyl, different benzothiazolyl, Ben Bing Evil Oxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, imidazopyridyl, imidazopyrimidine base and azepine carbazyl,

Wherein, Q₃₁To Q₃₃Can be with same as described above.

In one or more embodiments, main body can include alkaline earth compoundses.For example, main body can be selected from Be complexs (for example, compound H55), Mg complexs and Zn complexs.

In addition to the heterocyclic compound represented by formula 1, main body can be included from such as 9,10- bis- (2- naphthyls) anthracene (ADN), 2- methyl -9,10- double (naphthalene -2- bases) anthracene (MADN), 9,10- bis--(2- the naphthyls) -2- tert-butyl groups-anthracene (TBADN), 4, 4'- double (N- carbazyls) -1,1'- biphenyl (CBP), -9- carbazyls benzene (mCP) of 1,3- bis-, 1,3,5- tri- (carbazole -9- bases) benzene (TCP) and at least one that is selected into compound H55 of compound H1, but embodiment not limited to this：

In addition to the heterocyclic compound of the compound represented by formula 1, dopant can also include phosphorescent dopants or glimmering Photodopant.

Phosphorescent dopants can include the organometallic complex represented by following formula 401：

M(L₄₀₁)_xc1(L₄₀₂)_xc2

In formula 401 and formula 402,

M can be selected from iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh) and thulium (Tm),

L₄₀₁The part represented by formula 402 can be selected from, xc1 can be 1,2 or 3, wherein, when xc1 is two or bigger When, two or more L₄₀₁Can with mutually the same or different from each other,

L₄₀₂Can be organic ligand, xc2 can be selected from 0 to 4 integer, wherein, when xc2 is two or bigger, two Individual or more L₄₀₂Can with mutually the same or different from each other,

X₄₀₁To X₄₀₄Nitrogen or carbon can independently be,

X₄₀₁And X₄₀₃It can be connected via singly-bound or double bond, X₄₀₂And X₄₀₄It can be connected via singly-bound or double bond,

A₄₀₁And A₄₀₂Can be independently selected from C₅-C₆₀Carbocylic radical or C₁-C₆₀Heterocyclic radical,

X₄₀₅Can be singly-bound, *-O-*', *-S-*', *-C (=O)-* ', *-N (Q₄₁₁)-*'、*-C(Q₄₁₁) (Q₄₁₂)-*'、*-C(Q₄₁₁)=C (Q₄₁₂)-*'、*-C(Q₄₁₁)=* ' or *=C=*', wherein, Q₄₁₁And Q₄₁₂Can be hydrogen, deuterium, C₁-C₂₀Alkyl, C₁-C₂₀Alkoxy, phenyl, xenyl, terphenyl or naphthyl,

X₄₀₆Can be singly-bound, O or S,

R₄₀₁And R₄₀₂Can be independently selected from hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, hydrazine Base, hydrazone group, substituted or unsubstituted C₁-C₂₀Alkyl, substituted or unsubstituted C₁-C₂₀Alkoxy, substituted or unsubstituted C₃-C₁₀ Cycloalkyl, substituted or unsubstituted C₁-C₁₀Heterocyclylalkyl, substituted or unsubstituted C₃-C₁₀It is cycloalkenyl group, substituted or unsubstituted C₁-C₁₀Heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₆-C₆₀Aryloxy group, substitution or unsubstituted C₆-C₆₀Arylthio, substituted or unsubstituted C₁-C₆₀Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensation polycyclic base, take Generation or unsubstituted monovalent non-aromatic are condensed miscellaneous more ring groups ,-Si (Q₄₀₁)(Q₄₀₂)(Q₄₀₃)、-N(Q₄₀₁)(Q₄₀₂)、-B(Q₄₀₁) (Q₄₀₂) ,-C (=O) (Q₄₀₁) ,-S (=O)₂(Q₄₀₁) and-P (=O) (Q₄₀₁)(Q₄₀₂), wherein, Q₄₀₁To Q₄₀₃Can independently Selected from C₁-C₁₀Alkyl, C₁-C₁₀Alkoxy, C₆-C₂₀Aryl and C₁-C₂₀Heteroaryl,

Xc11 and xc12 can independently be selected from 0 to 10 integer, and

* and * ' in formula 402 represent the bound site with the M in formula 401.

In one embodiment, the A in formula 402₄₀₁And A₄₀₂Can be independently selected from phenyl, naphthyl, fluorenyl, spiral shell two Fluorenyl, indenyl, pyrrole radicals, thienyl, furyl, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyls, Pyridine radicals, pyrazinyl, pyrimidine radicals, pyridazinyl, quinolyl, isoquinolyl, benzoquinoline base, quinoxalinyl, quinazolyl, carbazole Base, benzimidazolyl, benzofuranyl, benzothienyl, isobenzo-thienyl, benzoxazolyl, Yi benzoxazolyls, triazole Base, tetrazole radical, oxadiazolyls, triazine radical, dibenzofuran group and dibenzothiophenes base.

In one or more embodiments, in formula 402, i) X₄₀₁Can be nitrogen, X₄₀₂Can be carbon, or ii) X₄₀₁ And X₄₀₂Can be nitrogen simultaneously.

In one or more embodiments, the R in formula 402₄₀₁And R₄₀₂Can independently selected from：

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, phenyl, naphthalene The C of at least one of base, cyclopenta, cyclohexyl, adamantyl, norborneol alkyl and norbornene₁-C₂₀Alkyl and C₁- C₂₀Alkoxy；

Cyclopenta, cyclohexyl, adamantyl, norborneol alkyl, norbornene, phenyl, xenyl, terphenyl, naphthalene Base, fluorenyl, pyridine radicals, pyrazinyl, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinolyl, quinoxalinyl, quinazolyl, Carbazyl, dibenzofuran group and dibenzothiophenes base；

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkane Base, C₁-C₂₀Alkoxy, cyclopenta, cyclohexyl, adamantyl, norborneol alkyl, norbornene, phenyl, xenyl, three Phenyl, naphthyl, fluorenyl, pyridine radicals, pyrazinyl, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinolyl, quinoxalinyl, quinoline The cyclopenta of at least one of oxazoline base, carbazyl, dibenzofuran group and dibenzothiophenes base, cyclohexyl, adamantyl, Norborneol alkyl, norbornene, phenyl, xenyl, terphenyl, naphthyl, fluorenyl, pyridine radicals, pyrazinyl, pyrimidine radicals, rattle away Piperazine base, triazine radical, quinolyl, isoquinolyl, quinoxalinyl, quinazolyl, carbazyl, dibenzofuran group and dibenzothiophenes Base；And

-Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃)、-N(Q₄₀₁)(Q₄₀₂)、-B(Q₄₀₁)(Q₄₀₂) ,-C (=O) (Q₄₀₁) ,-S (=O)₂ (Q₄₀₁) and-P (=O) (Q₄₀₁)(Q₄₀₂),

Wherein, Q₄₀₁To Q₄₀₃Can be independently selected from C₁-C₁₀Alkyl, C₁-C₁₀Alkoxy, phenyl, xenyl and naphthalene Base, but not limited to this.

In one or more embodiments, when the xc1 in formula 401 is two or bigger, two or more L₄₀₁In Two A₄₀₁Can be selectively via the X as linker₄₀₇It is connected to each other, or two or more L₄₀₁In two A₄₀₂ Can be selectively via the X as linker₄₀₈It is connected to each other (see compound PD1 to compound PD4 and compound PD7). X₄₀₇And X₄₀₈Singly-bound, *-O-*', *-S-*', *-C (=O)-* ', *-N (Q can independently be₄₁₃)-*'、*-C(Q₄₁₃) (Q₄₁₄)-* ' or *-C (Q₄₁₃)=C (Q₄₁₄)-* ' (wherein, Q₄₁₃And Q₄₁₄Hydrogen, deuterium, C can independently be₁-C₂₀Alkyl, C₁- C₂₀Alkoxy, phenyl, xenyl, terphenyl or naphthyl), but not limited to this.

L in formula 401₄₀₂Can be monovalent organic ligand, divalence organic ligand or trivalent organic ligand.For example, L₄₀₂Can With selected from halogen, diketone (for example, acetylacetone,2,4-pentanedione), carboxylic acid (for example, pyridine carboxylic acid) ,-C (=O), isonitrile ,-CN and phosphorus (example Such as, phosphine or phosphite), but embodiment not limited to this.

In one or more embodiments, phosphorescent dopants can be selected from such as compound PD1 to compound PD25, But embodiment not limited to this：

Fluorescent dopants can include novel arylamine compound or styrylamine compounds.

Fluorescent dopants can include the compound represented by following formula 501.

In formula 501,

Ar₅₀₁Can be substituted or unsubstituted C₅-C₆₀Carbocylic radical or substituted or unsubstituted C₁-C₆₀Heterocyclic radical,

L₅₀₁To L₅₀₃Can be independently selected from substituted or unsubstituted C₃-C₁₀It is cycloalkylidene, substituted or unsubstituted C₁-C₁₀Sub- Heterocyclylalkyl, substituted or unsubstituted C₃-C₁₀Sub- cycloalkenyl group, substituted or unsubstituted C₁-C₁₀Sub- heterocycloalkenyl, take Generation or unsubstituted C₆-C₆₀Arlydene, substituted or unsubstituted C₁-C₆₀Inferior heteroaryl, substituted or unsubstituted divalence are non-aromatic Condensation polycyclic base and the non-aromatic miscellaneous more ring groups of condensation of substituted or unsubstituted divalence,

Xd1 to xd3 can independently 0 to 3 integer；

R₅₀₁And R₅₀₂Can be independently selected from substituted or unsubstituted C₃-C₁₀Cycloalkyl, substituted or unsubstituted C₁- C₁₀Heterocyclylalkyl, substituted or unsubstituted C₃-C₁₀Cycloalkenyl group, substituted or unsubstituted C₁-C₁₀Heterocycloalkenyl, substitution or unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₆-C₆₀Aryloxy group, substituted or unsubstituted C₆-C₆₀Arylthio, substitution or unsubstituted C₁-C₆₀Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensation polycyclic base and the contracting of substituted or unsubstituted monovalent non-aromatic Miscellaneous more ring groups are closed, and

Xd4 can be 1 to 6 integer.

In one embodiment, the Ar in formula 501₅₀₁It can be selected from：

It is naphthyl, heptalene base, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, that non-alkenyl, phenanthryl, anthryl, glimmering Anthryl, benzo [9,10] phenanthryl, pyrenyl,Base, aphthacene Ji, Pi base, base, pentaphene base, indeno anthryl and indeno phenanthryl； And

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkane Base, C₁-C₂₀Naphthyl, heptalene base, fluorenyl, the spiral shell of at least one of alkoxy, phenyl, xenyl, terphenyl and naphthyl Two fluorenyls, benzo fluorenyl, dibenzo fluorenyl, that non-alkenyl, phenanthryl, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl, Base, aphthacene Ji, Pi base, base, pentaphene base, indeno anthryl and indeno phenanthryl.

In one or more embodiments, the L in formula 501₅₀₁To L₅₀₃Can independently selected from：

Phenylene, naphthylene, fluorenylidene, the fluorenyl of sub- spiral shell two, sub- benzo fluorenyl, sub- dibenzo fluorenyl, phenanthrylene, sub- anthracene Base, sub- fluoranthene base, sub- benzo [9,10] phenanthryl, sub- pyrenyl, AsiaBase, subunit, sub- pentaphene base, sub- hexacene base, Asia and five Phenyl, sub- thienyl, furylidene, sub- carbazyl, sub- indyl, sub- isoindolyl, sub- benzofuranyl, sub- benzothiophene Base, sub- dibenzofuran group, sub- dibenzothiophenes base, sub- benzo carbazole base, sub- dibenzo-carbazole base, sub- dibenzo thiophene cough up base and Sub- pyridine radicals；And

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkane Base, C₁-C₂₀Alkoxy, phenyl, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, phenanthrene Base, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, base, pentaphene base, hexacene base, pentacene base, thiophene Base, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzo thiophene Fen base, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene cough up the phenylene of at least one of base and pyridine radicals, naphthylene, Fluorenylidene, the fluorenyl of sub- spiral shell two, sub- benzo fluorenyl, sub- dibenzo fluorenyl, phenanthrylene, anthrylene, sub- fluoranthene base, sub- benzo [9,10] Phenanthryl, sub- pyrenyl, AsiaBase, subunit, sub- pentaphene base, sub- hexacene base, sub- pentacene base, sub- thienyl, furylidene, Asia Carbazyl, sub- indyl, sub- isoindolyl, sub- benzofuranyl, sub- benzothienyl, sub- dibenzofuran group, sub- dibenzo Thienyl, sub- benzo carbazole base, sub- dibenzo-carbazole base, sub- dibenzo thiophene cough up base and sub- pyridine radicals.

In one or more embodiments, the R in formula 502₅₀₁And R₅₀₂Can independently selected from：

Phenyl, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthracene Base, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, base, pentaphene base, hexacene base, pentacene base, thienyl, furans Base, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzene And carbazyl, dibenzo-carbazole base, dibenzo thiophene cough up base and pyridine radicals；And

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkane Base, C₁-C₂₀Alkoxy, phenyl, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, phenanthrene Base, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, base, pentaphene base, hexacene base, pentacene base, thiophene Base, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzo thiophene Fen base, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene cough up base, pyridine radicals and-Si (Q₃₁)(Q₃₂)(Q₃₃) at least one It is the phenyl of person, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, glimmering Anthryl, benzo [9,10] phenanthryl, pyrenyl,Base, base, pentaphene base, hexacene base, pentacene base, thienyl, furyl, click Oxazolyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole Base, dibenzo-carbazole base, dibenzo thiophene cough up base and pyridine radicals,

Wherein, Q₃₁To Q₃₃It can be selected from C₁-C₁₀Alkyl, C₁-C₁₀Alkoxy, phenyl, xenyl, terphenyl and Naphthyl.

In one or more embodiments, the xd4 in formula 501 can be 2, but embodiment not limited to this.

For example, fluorescent dopants can be selected from compound FD1 to compound FD22：

In one or more embodiments, fluorescent dopants can be selected from following compound, but embodiment is not It is limited to this.

Electron transporting zone can have：I) single layer structure, it includes the individual layer comprising single material；Ii) single layer structure, It includes the individual layer for including a variety of different materials；Or iii) sandwich construction, it has the multiple layers for including a variety of different materials.

Electron transporting zone can include noting from cushion, hole blocking layer, Electronic Control layer, electron transfer layer and electronics Enter and at least one, but embodiment not limited to this is selected in layer.

For example, electron transporting zone can have electron transfer layer/electron injection Rotating fields, hole blocking layer/electronics to pass Defeated layer/electron injection Rotating fields, Electronic Control layer/electron transfer layer/electron injection Rotating fields or cushion/electric transmission Layer/electron injection Rotating fields, wherein, for every kind of structure, composition layer is sequentially stacked from emission layer.However, electric transmission area The embodiment not limited to this of the structure in domain.

Electron transporting zone is (for example, cushion, hole blocking layer, Electronic Control layer or electronics in electron transporting zone Transport layer) (the π electron-depleted nitrogen- containing azo-cycle comprising at least one poor pi-electron can be included Containing ring, or pi-electron exhaust contain azo-cycle) without metallic compound.

" the containing azo-cycle of poor pi-electron " is represented with C of at least one *-N=*' parts as loop portion₁-C₆₀Heterocycle Base.

For example, " the containing azo-cycle of poor pi-electron " can be i) miscellaneous monocyclic with 5 yuan to 7 yuan of at least one *-N=*' parts Group, ii) be respectively provided with least one *-N=*' parts two or more 5 yuan to 7 yuan heteromonocyclic groups group be condensed each other it is miscellaneous Polycyclic moiety or iii) be respectively provided with least one *-N=*' parts 5 yuan to 7 yuan heteromonocyclic groups group in it is at least one with extremely A few C₅-C₆₀The miscellaneous polycyclic moiety of carbocylic radical condensation.

The example containing azo-cycle of poor pi-electron include imidazoles, pyrazoles, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, Pyrimidine, pyridazine, indazole, purine, quinoline, isoquinolin, benzoquinoline, phthalazines, naphthyridines, quinoxaline, quinazoline, cinnolines, phenanthridines, a word used for translation Pyridine, phenanthroline, azophenlyene, benzimidazole, different benzothiazole, benzoxazole, Yi benzoxazoles, triazole, tetrazolium, oxadiazoles, triazine, Thiadiazoles, imidazopyridine, imidazopyrimidine and azepine carbazole, but not limited to this.

In one embodiment, in addition to the heterocyclic compound represented by formula 1, electron transporting zone can also include by The compound that formula 601 represents.

[Ar₆₀₁]_xe11-[(L₆₀₁)_xe1-R₆₀₁]_xe21。

In formula 601,

Ar₆₀₁Can be substituted or unsubstituted C₅-C₆₀Carbocylic radical or substituted or unsubstituted C₁-C₆₀Heterocyclic radical,

Xe11 can be 1,2 or 3,

L₆₀₁Substituted or unsubstituted C can be selected from₃-C₁₀Cycloalkylidene, substituted or unsubstituted C₁-C₁₀Sub- heterocycle alkane Base, substituted or unsubstituted C₃-C₁₀Sub- cycloalkenyl group, substituted or unsubstituted C₁-C₁₀It is sub- heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Arlydene, substituted or unsubstituted C₁-C₆₀The non-aromatic condensation polycyclic base of inferior heteroaryl, substituted or unsubstituted divalence and The substituted or unsubstituted non-aromatic miscellaneous more ring groups of condensation of divalence；

Xe1 can be selected from 0 to 5 integer,

R₆₀₁Substituted or unsubstituted C can be selected from₃-C₁₀Cycloalkyl, substituted or unsubstituted C₁-C₁₀Heterocyclylalkyl, take Generation or unsubstituted C₃-C₁₀Cycloalkenyl group, substituted or unsubstituted C₁-C₁₀Heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Aryl, Substituted or unsubstituted C₆-C₆₀Aryloxy group, substituted or unsubstituted C₆-C₆₀Arylthio, substituted or unsubstituted C₁-C₆₀Heteroaryl Base, substituted or unsubstituted monovalent non-aromatic condensation polycyclic base, substituted or unsubstituted monovalent non-aromatic be condensed miscellaneous more ring groups ,- Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃) ,-C (=O) (Q₆₀₁) ,-S (=O)₂(Q₆₀₁) and-P (=O) (Q₆₀₁)(Q₆₀₂),

Q₆₀₁To Q₆₀₃C can independently be₁-C₁₀Alkyl, C₁-C₁₀Alkoxy, phenyl, xenyl, terphenyl or naphthalene Base,

Xe21 can be selected from 1 to 5 integer.

In one embodiment, the Ar of xe11 number₆₀₁In at least one and/or xe21 number R₆₀₁In at least one It is individual to contain azo-cycle including poor pi-electron.

In one embodiment, the ring Ar in formula 601₆₀₁It can be selected from：

Phenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, that non-alkenyl, phenanthryl, anthryl, fluoranthene Base, benzo [9,10] phenanthryl, pyrenyl,Base, aphthacene Ji, Pi base, base, pentaphene base, indeno anthryl, dibenzofuran group, Dibenzothiophenes base, carbazyl, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyls, pyridine radicals, pyrazine Base, pyrimidine radicals, pyridazinyl, indazolyl, purine radicals, quinolyl, isoquinolyl, benzoquinoline base, phthalazinyl, naphthyridines base, quinoline Quinoline base, quinazolyl, cinnolines base, phenanthridinyl, acridinyl, phenanthroline, phenazinyl, benzimidazolyl, different benzothiazolyl, benzene Bing oxazolyls, Yi benzoxazolyls, triazolyl, tetrazole radical, oxadiazolyls, triazine radical, thiadiazolyl group, imidazopyridyl, miaow Azoles and pyrimidine radicals and azepine carbazyl；And

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkane Base, C₁-C₂₀Alkoxy, phenyl, xenyl, terphenyl, naphthyl ,-Si (Q₃₁)(Q₃₂)(Q₃₃) ,-S (=O)₂(Q₃₁) and-P (= O)(Q₃₁)(Q₃₂) at least one of phenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, that non-alkene Base, phenanthryl, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, aphthacene Ji, Pi base, base, pentaphene base, indeno It is anthryl, dibenzofuran group, dibenzothiophenes base, carbazyl, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazolyls, different Oxazolyl, pyridine radicals, pyrazinyl, pyrimidine radicals, pyridazinyl, indazolyl, purine radicals, quinolyl, isoquinolyl, benzoquinoline base, Phthalazinyl, naphthyridines base, quinoxalinyl, quinazolyl, cinnolines base, phenanthridinyl, acridinyl, phenanthroline, phenazinyl, benzimidazole Base, different benzothiazolyl, benzoxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, oxadiazolyls, triazine radical, thiadiazoles Base, imidazopyridyl, imidazopyrimidine base and azepine carbazyl,

When the xe11 in formula 601 is two or bigger, two or more Ar₆₀₁It can be connected to each other via singly-bound.

In one or more embodiments, the Ar in formula 601₆₀₁It can be anthryl.

In one or more embodiments, the compound represented by formula 601 can be represented by formula 601-1：

In formula 601-1,

X₆₁₄Can be N or C (R₆₁₄), X₆₁₅Can be N or C (R₆₁₅), X₆₁₆Can be N or C (R₆₁₆), from X₆₁₄To X₆₁₆In At least one of selection can be N,

L₆₁₁To L₆₁₃Can independently with reference to L₆₀₁What is described is substantially the same,

Xe611 to xe613 can be independently substantially the same with combination xe1 descriptions,

R₆₁₁To R₆₁₃Can independently with reference to R₆₀₁What is described is substantially the same,

R₆₁₄To R₆₁₆Can be independently selected from hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, hydrazine Base, hydrazone group, C₁-C₂₀Alkyl, C₁-C₂₀Alkoxy, phenyl, xenyl, terphenyl and naphthyl.

In one embodiment, the L in formula 601 and formula 601-1₆₀₁And L₆₁₁To L₆₁₃Can independently selected from：

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkane Base, C₁-C₂₀Alkoxy, phenyl, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, phenanthrene Base, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, base, pentaphene base, hexacene base, pentacene base, thiophene Base, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzo thiophene Fen base, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene cough up base, pyridine radicals, imidazole radicals, pyrazolyl, thiazolyl, isothiazole Ji, oxazolyl, isoxazolyls, thiadiazolyl group, oxadiazolyls, pyrazinyl, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinoline Quinoline base, benzoquinoline base, phthalazinyl, naphthyridines base, quinoxalinyl, quinazolyl, cinnolines base, phenanthridinyl, acridinyl, phenanthroline Base, phenazinyl, benzimidazolyl, different benzothiazolyl, benzoxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, imidazoles And the phenylene, naphthylene, fluorenylidene, the fluorenes of sub- spiral shell two of at least one of pyridine radicals, imidazopyrimidine base and azepine carbazyl Base, sub- benzo fluorenyl, sub- dibenzo fluorenyl, phenanthrylene, anthrylene, sub- fluoranthene base, sub- benzo [9,10] phenanthryl, sub- pyrenyl, AsiaBase, subunit, sub- pentaphene base, sub- hexacene base, sub- pentacene base, sub- thienyl, furylidene, sub- carbazyl, sub- indoles Base, sub- isoindolyl, sub- benzofuranyl, sub- benzothienyl, sub- dibenzofuran group, sub- dibenzothiophenes base, sub- benzo Carbazyl, sub- dibenzo-carbazole base, sub- dibenzo thiophene cough up base, sub- pyridine radicals, sub- imidazole radicals, sub- pyrazolyl, sub- thiazolyl, sub- different Thiazolyl, Ya oxazolyls, Ya isoxazolyls, sub- thiadiazolyl group, Ya oxadiazolyls, sub- pyrazinyl, sub- pyrimidine radicals, sub- pyridazinyl, Sub- triazine radical, sub- quinolyl, sub- isoquinolyl, sub- benzoquinoline base, sub- phthalazinyl, sub- naphthyridines base, sub- quinoxalinyl, sub- quinoline azoles Quinoline base, sub- cinnolines base, sub- phenanthridinyl, sub- acridinyl, sub- phenanthroline, sub- phenazinyl, sub- benzimidazolyl, sub- different benzothiazole Base, sub- benzoxazolyl, sub- Yi benzoxazolyls, sub- triazolyl, sub- tetrazole radical, sub- imidazopyridyl, sub- imidazopyrimidine Base and sub- azepine carbazyl, but not limited to this.

But embodiment not limited to this.

In one or more embodiments, formula 601 and xe1 in formula 601-1 and xe611 to xe613 can be independent Ground is 0,1 or 2.

In one or more embodiments, the R in formula 601 and formula 601-1₆₀₁And R₆₁₁To R₆₁₃Can independently it select From in：

Phenyl, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthracene Base, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, base, pentaphene base, hexacene base, pentacene base, thienyl, furans Base, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzene And carbazyl, dibenzo-carbazole base, dibenzo thiophene cough up base, pyridine radicals, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazoles Base, isoxazolyls, thiadiazolyl group, oxadiazolyls, pyrazinyl, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinolyl, benzene And quinolyl, phthalazinyl, naphthyridines base, quinoxalinyl, quinazolyl, cinnolines base, phenanthridinyl, acridinyl, phenanthroline, azophenlyene Base, benzimidazolyl, different benzothiazolyl, benzoxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, imidazopyridine Base, imidazopyrimidine base and azepine carbazyl；

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkane Base, C₁-C₂₀Alkoxy, phenyl, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, phenanthrene Base, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, base, pentaphene base, hexacene base, pentacene base, thiophene Base, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzo thiophene Fen base, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene cough up base, pyridine radicals, imidazole radicals, pyrazolyl, thiazolyl, isothiazole Ji, oxazolyl, isoxazolyls, thiadiazolyl group, oxadiazolyls, pyrazinyl, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinoline Quinoline base, benzoquinoline base, phthalazinyl, naphthyridines base, quinoxalinyl, quinazolyl, cinnolines base, phenanthridinyl, acridinyl, phenanthroline Base, phenazinyl, benzimidazolyl, different benzothiazolyl, benzoxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, imidazoles And the phenyl, xenyl, terphenyl, naphthyl, fluorenes of at least one of pyridine radicals, imidazopyrimidine base and azepine carbazyl Base, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, Base, pentaphene base, hexacene base, pentacene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, Benzothienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene cough up base, pyrrole Piperidinyl, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyls, thiadiazolyl group, oxadiazolyls, pyrazinyl, Pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinolyl, benzoquinoline base, phthalazinyl, naphthyridines base, quinoxalinyl, quinazoline It is base, cinnolines base, phenanthridinyl, acridinyl, phenanthroline, phenazinyl, benzimidazolyl, different benzothiazolyl, benzoxazolyl, different Benzoxazolyl, triazolyl, tetrazole radical, imidazopyridyl, imidazopyrimidine base and azepine carbazyl；And

- S (=O)₂(Q₆₀₁) and-P (=O) (Q₆₀₁)(Q₆₀₂),

Wherein, Q₆₀₁And Q₆₀₂With same as described above.

Electron transporting zone can include at least one chemical combination for example selected from compound ET1 into compound ET36 Thing, but embodiment not limited to this：

In one or more embodiments, electron transporting zone can include for example from 2,9- dimethyl -4,7- hexichol Base -1,10- phenanthroline (BCP), 4,7- diphenyl -1,10- phenanthroline (Bphen), Alq₃, BAlq, 3- (biphenyl -4- bases) -5- At least one selected in (4- tert-butyl-phenyls) -4- phenyl -4H-1,2,4- triazoles (TAZ) and NTAZ.

The thickness of cushion, hole blocking layer or Electronic Control layer can be independently for example aboutTo aboutIn the range of, for example, aboutTo aboutIn the range of.When cushion, hole blocking layer and electronics When the thickness of key-course is in the range of these, electron transporting zone can have excellent hole-blocking characteristics or Electronic Control special Property is without significantly increasing driving voltage.

The thickness of electron transfer layer can be for example aboutTo aboutIn the range of, for example, aboutTo aboutIn the range of.When in the range of the thickness of electron transfer layer is described above, electron transfer layer can With with gratifying electron transport property without significantly increasing driving voltage.

In addition to materials described above, electron transporting zone (for example, electron transfer layer in electron transporting zone) Such as material comprising metal can also be included.

Material comprising metal can include for example selecting at least from alkali metal complex and alkaline earth compoundses It is a kind of.Alkali metal complex can include the metal for example selected from Li ions, Na ions, K ions, Rb ions and Cs ions Ion, alkaline earth compoundses can include what is for example selected from Be ions, Mg ions, Ca ions, Sr ions and Ba ions Metal ion.Such as hydroxyl can be selected from alkali metal complex or the part of the metallic ion coordination of alkaline earth compoundses Quinoline, isoquinolinol, hydroxy benzo quinoline, hydroxy-acridine, hydroxyl phenanthridines, Qiang base Ben Ji oxazoles, hydroxy phenyl thiazole, hydroxyl Er Ben oxadiazoles, hydroxy diphenyl thiadiazoles, Qiang base Ben oxadiazoles, hydroxy phenyl thiadiazoles, hydroxy phenyl pyridine, hydroxyl Phenylbenzimidazol, hydroxy phenyl benzothiazole, bipyridyl, phenanthroline and cyclopentadiene, but embodiment not limited to this.

For example, the material comprising metal can include Li complexs.Li complexs can include such as compound ET-D1 (oxyquinoline lithium, LiQ) or ET-D2.

Electron transporting zone can include promoting electronics from the injected electrons implanted layer of second electrode 190.For example, electronics is noted Second electrode 190 can directly be contacted by entering layer.

Electron injecting layer can have for example：I) single layer structure, it includes the individual layer comprising single material；Ii) individual layer knot Structure, it includes the individual layer for including a variety of different materials；Or iii) sandwich construction, its have include the multiple of a variety of different materials Layer.

Electron injecting layer can include such as alkali metal, alkaline-earth metal, rare earth metal, alkali metal compound, alkaline-earth metal Compound, rare earth compound, alkali metal complex, alkaline earth compoundses, rare earth metal complex or theirs is any Combination.

Alkali metal can be selected from Li, Na, K, Rb and Cs.In one embodiment, alkali metal can be Li, Na or Cs. In one or more embodiments, alkali metal can be Li or Cs, but embodiment not limited to this.

Alkaline-earth metal can be selected from such as Mg, Ca, Sr and Ba.

Rare earth metal can be selected from such as Sc, Y, Ce, Yb, Gd and Tb.

Alkali metal compound, alkaline earth metal compound and rare earth compound can be selected from such as alkali metal, alkaline earth The oxide and halide (for example, fluoride, chloride, bromide or iodide) of metal and rare earth metal.

Alkali metal compound can be selected from such as alkali metal oxide (such as Li₂O、Cs₂O or K₂) and alkali metal halogenation O Thing (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI or RbI).In one embodiment, alkali metal compound can select From in LiF, Li₂O, NaF, LiI, NaI, CsI and KI, but embodiment not limited to this.

For example, alkaline earth metal compound can be selected from such as BaO, SrO, CaO, Ba_xSr_1-xO(0<x<Or Ba 1)_xCa_1-xO (0<x<1) alkaline earth metal compound.In one embodiment, alkaline earth metal compound can be selected from BaO, SrO and CaO, But embodiment not limited to this.

Rare earth compound can be selected from such as YbF₃、ScF₃、ScO₃、Y₂O₃、Ce₂O₃、GdF₃And TbF₃.At one In embodiment, rare earth compound can be selected from YbF₃、ScF₃、TbF₃、YbI₃、ScI₃And TbI₃, but embodiment is unlimited In this.

For example, alkali metal complex, alkaline earth compoundses and rare earth metal complex can be included as described above The ion of alkali metal, alkaline-earth metal and rare earth metal, with alkali metal complex, alkaline earth compoundses and rare earth metal complex The part of metallic ion coordination can be independently selected from oxyquinoline, isoquinolinol, hydroxy benzo quinoline, hydroxyl a word used for translation Pyridine, hydroxyl phenanthridines, Qiang base Ben Ji oxazoles, hydroxy phenyl thiazole, Qiang base Er Ben oxadiazoles, hydroxy diphenyl thiadiazoles, hydroxyl Ben oxadiazoles, hydroxy phenyl thiadiazoles, hydroxy phenyl pyridine, hydroxy phenyl benzimidazole, hydroxy phenyl benzothiazole, connection pyrrole Pyridine, phenanthroline and cyclopentadiene, but embodiment not limited to this.

For example, electron injecting layer can be or can include alkali metal as described above, alkaline-earth metal, rare earth metal, Alkali metal compound, alkaline earth metal compound, rare earth compound, alkali metal complex, alkaline earth compoundses, rare earth gold Metal complex or their any combination.In one or more embodiments, electron injecting layer can also include organic material. When electron injecting layer also includes organic material, then such as alkali metal, alkaline-earth metal, rare earth metal, alkali metal compound, alkaline earth Metallic compound, rare earth compound, alkali metal complex, alkaline earth compoundses, rare earth metal complex or they Any combination can be uniformly or non-uniformly dispersed in the matrix including organic material.

The thickness of electron injecting layer can be for example aboutTo aboutIn the range of, for example, aboutExtremely AboutIn the range of.When in the range of the thickness of electron injecting layer is described above, electron injecting layer can have order The Electron Injection Characteristics of people's satisfaction are without significantly increasing driving voltage.

Second electrode 190 can be arranged on the organic layer 150 having a structure in which.Second electrode 190 can be made For the negative electrode of electron injection electrode, on this point, the material for forming second electrode 190 can be for example with low effusion The material of work(, such material can be metal, alloy, conductive compound or their mixture.

Second electrode 190 can be included for example from lithium (Li), silver-colored (Ag), magnesium (Mg), aluminium (Al), aluminium-lithium (Al-Li), calcium (Ca), at least one selected in magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO and IZO, but embodiment not limited to this.The Two electrodes 190 can be transmission electrode, half transmitting electrode or reflecting electrode.

Second electrode 190 can have single layer structure or the sandwich construction including two or more layers.

In Fig. 2 example organic luminescent device 20, organic luminescent device 20 includes with the order of order of the statement heap Folded the first coating 210, first electrode 110, organic layer 150 and second electrode 190, Fig. 3 example organic luminescent device 30 wrap The first electrode 110 stacked with the order of order of the statement, organic layer 150, the coating 220 of second electrode 190 and second are included, is schemed The first coating 210 that 4 example organic luminescent device 40 includes stacking with the order of order of the statement, first electrode 110, have Machine layer 150, the coating 220 of second electrode 190 and second.

On Fig. 2 to Fig. 4, first electrode 110, organic layer 150 can be understood by referring to the description provided with reference to Fig. 1 With second electrode 190.

In each organic layer 150 in organic luminescent device 20 and 40, caused light can be towards outer in emission layer Portion is through the coating 210 of first electrode 110 and first as half transmitting electrode or transmission electrode, in organic luminescent device 30 and 40 In each organic layer 150 in, in emission layer caused light can towards outside pass through as half transmitting electrode or transmission electricity The coating 220 of second electrode 190 and second of pole.

First coating 210 and the second coating 220 can improve external light emission efficiency according to the principle of constructive interference.

First coating 210 and the second coating 220 can independently be organic coating for example including organic material including The inorganic coating of inorganic material or the composite coating including organic material and inorganic material.

Selected from the first coating 210 and the second coating 220 it is at least one can independently include for example from carbocyclic ring Compound, heterocyclic compound, aminated compounds, derivatives of porphyrin, phthalocyanine derivates, naphthalene cyanines derivative, alkali metal complex and At least one material selected in alkaline earth compoundses.Carbocyclic compound, heterocyclic compound and aminated compounds can be with optional Substituting with selecting has the substituent for including at least one element selected from O, N, S, Se, Si, F, Cl, Br and I.In an implementation In example, what is selected from the first coating 210 and the second coating 220 at least one can independently include aminated compounds.

In one embodiment, selected from the first coating 210 and the second coating 220 it is at least one can independently Including the compound represented by formula 201 or the compound represented by formula 202.

In one or more embodiments, selected from the first coating 210 and the second coating 220 it is at least one can be with Independently include the compound that from such as compound HT28 to compound HT33 and compound CP1 selects into compound CP5, But embodiment not limited to this.

Hereinbefore, combined Fig. 1 to Fig. 4 describes the organic luminescent device according to embodiment.However, embodiment is not It is limited to this.

Can be by using for example from vacuum moulding machine, spin coating, casting, Lang Gemiaoer-Blodget (LB) depositions, ink-jet print The suitable methods of one or more that are selected in brush, laser printing and laser induced thermal imaging form structure in a particular area Into the layer of hole transporting zone, emission layer and the layer for forming electron transporting zone.

When by depositing to form each layer of each layer of hole transporting zone, emission layer and electron transporting zone, , can be at such as about 100 DEG C extremely by view of for forming the compound of layer to be deposited and the structure of layer to be formed About 500 DEG C of depositing temperature, such as about 10^-8Hold in the palm to about 10^-3The vacuum of support and for example about/ the second is to aboutDeposition is performed under the sedimentation rate of/second.

Form each layer for forming hole transporting zone, emission layer when by spin coating and form each of electron transporting zone During individual layer, according in layer by including compound and each layer of structure to be formed, can be in such as about 2,000rpm extremely Spin coating is performed under about 5,000rpm coating speed and about 80 DEG C to about 200 DEG C of heat treatment temperature.

Term " C as used herein₁-C₆₀Alkyl " refers to the saturated fat with 1 straight or branched to 60 carbon atoms Fat hydrocarbon monoradical, its non-limiting example include methyl, ethyl, propyl group, isobutyl group, sec-butyl, the tert-butyl group, amyl group, isoamyl Base and hexyl.Term " C as used herein₁-C₆₀Alkylidene " refers to and C₁-C₆₀Alkyl has the divalent group of identical structure.

Term " C as used herein₂-C₆₀Alkenyl " refers to by C₂-C₆₀The centre of alkyl or end substitution have at least One carbon-to-carbon double bond and the alkyl formed, its non-limiting example include vinyl, acrylic and cyclobutenyl.As used herein Term " C₂-C₆₀Alkenylene " refers to and C₂-C₆₀Alkenyl has the divalent group of identical structure.

Term " C as used herein₂-C₆₀Alkynyl " refers to by C₂-C₆₀The centre of alkyl or end substitution have at least One carbon-to-carbon triple bond and the alkyl formed, its non-limiting example include acetenyl and propinyl.Term as used herein “C₂-C₆₀Alkynylene " refers to and C₂-C₆₀Alkynyl has the divalent group of identical structure.

Term " C as used herein₁-C₆₀Alkoxy " refers to by-OA₁₀₁(wherein, A₁₀₁For C₁-C₆₀Alkyl) represent unit price Group, its non-limiting example include methoxyl group, ethyoxyl and isopropoxy.

Term " C as used herein₃-C₁₀Cycloalkyl " refers to 3 monocyclic bases of the monovalent saturated hydrocarbon to 10 carbon atoms Group, its non-limiting example include cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl and suberyl.Term " C as used herein₃- C₁₀Cycloalkylidene " refers to and C₃-C₁₀Cycloalkyl has the divalent group of identical structure.

Term " C as used herein₁-C₁₀Heterocyclylalkyl " refers to have to be selected as ring member nitrogen atoms from N, O, Si, P and S The monovalent saturation monocyclic groups of at least one hetero atom selected and 1 to 10 carbon atom, its non-limiting example include 1, 2,3,4- oxatriazoles alkyl, tetrahydrofuran base and tetrahydro-thienyl.Term " C as used herein₁-C₁₀Sub- Heterocyclylalkyl " refer to C₁-C₁₀Heterocyclylalkyl has the divalent group of identical structure.

Term " C as used herein₃-C₁₀Cycloalkenyl group " refers to has 3 to 10 carbon atoms and at least one in its ring Carbon-to-carbon double bond and without armaticity monovalent monocyclic group, its non-limiting example include cyclopentenyl, cyclohexenyl group and Cycloheptenyl.Term " C as used herein₃-C₁₀Sub- cycloalkenyl group " refers to and C₃-C₁₀Cycloalkenyl group has the bilvalent radical of identical structure Group.

Term " C as used herein₁-C₁₀Heterocycloalkenyl " refers to be had as ring member nitrogen atoms from N, O, Si, P in its ring With the monovalent monocyclic group of at least one hetero atom selected in S, 1 to 10 carbon atom and at least one double bond.C₁-C₁₀ The non-limiting example of heterocycloalkenyl is 4,5- dihydro -1,2,3,4- oxatriazoles base, 2,3 dihydro furan base and 2,3- dihydro thiophenes Fen base.Term " C as used herein₁-C₁₀Sub- heterocycloalkenyl " refers to and C₁-C₁₀Heterocycloalkenyl has the bilvalent radical of identical structure Group.

Term " C as used herein₆-C₆₀Aryl " refers to including 6 carbocyclic, aromatic systems to 60 carbon atoms Monoradical, term " C as used herein₆-C₆₀Arlydene ", which refers to have, includes 6 carbocyclic, aromatic systems to 60 carbon atoms Divalent group.C₆-C₆₀The non-limiting example of aryl include phenyl, naphthyl, anthryl, phenanthryl, pyrenyl andBase.Work as C₆-C₆₀ Aryl and C₆-C₆₀When arlydene each includes two or more rings, ring can condense each other.

Term " C as used herein₁-C₆₀Heteroaryl " refers to the monoradical with heteroaromatic system, the heteroaromatic System has at least one selected from N, O, Si, P and S as ring member nitrogen atoms in addition to 1 to 60 carbon atom Hetero atom.Term " C as used herein₁-C₆₀Inferior heteroaryl " refers to the divalent group with heteroaromatic system, the heteroaromatic System has at least one selected from N, O, Si, P and S as ring member nitrogen atoms in addition to 1 to 60 carbon atom Hetero atom.C₁-C₆₀The non-limiting example of heteroaryl includes pyridine radicals, pyrimidine radicals, pyrazinyl, pyridazinyl, triazine radical, quinolyl And isoquinolyl.Work as C₁-C₆₀Heteroaryl and C₁-C₆₀When inferior heteroaryl each includes two or more rings, ring can be thick each other Close.

Term " C as used herein₆-C₆₀Aryloxy group " refers to-OA₁₀₂(wherein, A₁₀₂For C₆-C₆₀Aryl), it is used herein Term " C₆-C₆₀Arylthio " refers to-SA₁₀₃(wherein, A₁₀₃For C₆-C₆₀Aryl).

Term " monovalent non-aromatic condensation polycyclic base " as used herein refer to two or more rings being condensed each other, Only ring member nitrogen atoms are used as with carbon atom (for example, with 8 to 60 carbon atoms) and in whole molecular structure with non-aromatic The monoradical of fragrance.The detailed example of monovalent non-aromatic condensation polycyclic base is fluorenyl." divalence is non-aromatic for term used herein Condensation polycyclic base " refers to the divalent group for having identical structure with monovalent non-aromatic condensation polycyclic base.

Term " monovalent non-aromatic is condensed miscellaneous more ring groups " as used herein, which refers to, has two or more being condensed each other Ring, with as ring member nitrogen atoms in addition to the carbon atom (for example, with 1 to 60 carbon atom) from N, O, Si, P and S At least one hetero atom of middle selection and there is nonaromatic monoradical in whole molecular structure.Monovalent non-aromatic is condensed The example of miscellaneous more ring groups is carbazyl.Term " the non-aromatic miscellaneous more ring groups of condensation of divalence " used herein refers to and contracted with monovalent non-aromatic Closing miscellaneous more ring groups has the divalent group of identical structure.

Term " C as used herein₅-C₆₀Carbocylic radical " refers to the monocyclic or polycyclic moiety with 5 to 60 carbon atoms, its In, ring member nitrogen atoms are only carbon atoms.C₅-C₆₀Carbocylic radical can be aromatic carbocyclic base or non-aromatic carbocylic radical.C₅-C₆₀Carbocylic radical can To be ring (such as benzene), monoradical (such as phenyl) or divalent group (such as phenylene).In one or more embodiments In, according to being connected to C₅-C₆₀The quantity of the substituent of carbocylic radical, C₅-C₆₀Carbocylic radical can be trivalent radical or quaternary groups.

Term " C as used herein₁-C₆₀Heterocyclic radical " refers to：Except using except carbon, (quantity of carbon atom can be at 1 extremely In the scope of 60) at least one hetero atom selected from N, O, Si, P and S as ring member nitrogen atoms outside, with C₁-C₆₀Carbon Ring group has the group of identical structure.

From substituted C₅-C₆₀Carbocylic radical, the C of substitution₁-C₆₀Heterocyclic radical, the C of substitution₃-C₁₀Cycloalkylidene, the C of substitution₁-C₁₀ Sub- Heterocyclylalkyl, the C of substitution₃-C₁₀Sub- cycloalkenyl group, the C of substitution₁-C₁₀Sub- heterocycloalkenyl, the C of substitution₆-C₆₀Arlydene, substitution C₁-C₆₀Inferior heteroaryl, the non-aromatic condensation polycyclic base of divalence of substitution, the non-aromatic condensation of the divalence of substitution miscellaneous more ring groups, substitution C₁-C₆₀Alkyl, the C of substitution₂-C₆₀Alkenyl, the C of substitution₂-C₆₀Alkynyl, the C of substitution₁-C₆₀Alkoxy, the C of substitution₃-C₁₀Cycloalkanes Base, the C of substitution₁-C₁₀Heterocyclylalkyl, the C of substitution₃-C₁₀Cycloalkenyl group, the C of substitution₁-C₁₀Heterocycloalkenyl, the C of substitution₆-C₆₀Aryl, Substituted C₆-C₆₀Aryloxy group, the C of substitution₆-C₆₀Arylthio, the C of substitution₁-C₆₀Heteroaryl, the monovalent non-aromatic condensation of substitution are more Ring group and the monovalent non-aromatic of substitution are condensed at least one substituent selected in the substituent of miscellaneous more ring groups and can be selected from：

Deuterium (- D) ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₆₀Alkyl, C₂-C₆₀Alkene Base, C₂-C₆₀Alkynyl and C₁-C₆₀Alkoxy；

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₃-C₁₀Ring Alkyl, C₁-C₁₀Heterocyclylalkyl, C₃-C₁₀Cycloalkenyl group, C₁-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl, C₆-C₆₀Aryloxy group, C₆-C₆₀Fragrant sulphur Base, C₁-C₆₀Heteroaryl, monovalent non-aromatic condensation polycyclic base, monovalent non-aromatic are condensed miscellaneous more ring groups ,-Si (Q₁₁)(Q₁₂)(Q₁₃)、- N(Q₁₁)(Q₁₂)、-B(Q₁₁)(Q₁₂) ,-C (=O) (Q₁₁) ,-S (=O)₂(Q₁₁) and-P (=O) (Q₁₁)(Q₁₂At least one of) C₁-C₆₀Alkyl, C₂-C₆₀Alkenyl, C₂-C₆₀Alkynyl and C₁-C₆₀Alkoxy；

C₃-C₁₀Cycloalkyl, C₁-C₁₀Heterocyclylalkyl, C₃-C₁₀Cycloalkenyl group, C₁-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl, C₆-C₆₀Virtue Epoxide, C₆-C₆₀Arylthio, C₁-C₆₀Heteroaryl, monovalent non-aromatic condensation polycyclic base and monovalent non-aromatic are condensed miscellaneous more ring groups；

C₃-C₁₀Cycloalkyl, C₁-C₁₀Heterocyclylalkyl, C₃-C₁₀Cycloalkenyl group, C₁-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl, C₆-C₆₀Virtue Epoxide, C₆-C₆₀Arylthio, C₁-C₆₀Heteroaryl, monovalent non-aromatic condensation polycyclic base and monovalent non-aromatic are condensed miscellaneous more ring groups；With And

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₆₀Alkane Base, C₂-C₆₀Alkenyl, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy, C₃-C₁₀Cycloalkyl, C₁-C₁₀Heterocyclylalkyl, C₃-C₁₀Cycloalkenyl group, C₁- C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl, C₆-C₆₀Aryloxy group, C₆-C₆₀Arylthio, C₁-C₆₀Heteroaryl, monovalent non-aromatic condensation polycyclic Base, monovalent non-aromatic are condensed miscellaneous more ring groups ,-Si (Q₂₁)(Q₂₂)(Q₂₃)、-N(Q₂₁)(Q₂₂)、-B(Q₂₁)(Q₂₂) ,-C (=O) (Q₂₁) ,-S (=O)₂(Q₂₁) and-P (=O) (Q₂₁)(Q₂₂) at least one of-Si (Q₃₁)(Q₃₂)(Q₃₃)、-N(Q₃₁) (Q₃₂)、-B(Q₃₁)(Q₃₂) ,-C (=O) (Q₃₁) ,-S (=O)₂(Q₃₁) and-P (=O) (Q₃₁)(Q₃₂),

Wherein, Q₁To Q₅、Q₁₁To Q₁₃、Q₂₁To Q₂₃And Q₃₁To Q₃₃Can independently selected from hydrogen, deuterium ,-F ,-Cl ,- Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₆₀Alkyl, C₂-C₆₀Alkenyl, C₂-C₆₀Alkynyl, C₁-C₆₀Alcoxyl Base, C₃-C₁₀Cycloalkyl, C₁-C₁₀Heterocyclylalkyl, C₃-C₁₀Cycloalkenyl group, C₁-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl, C₁-C₆₀Heteroaryl, Monovalent non-aromatic condensation polycyclic base, monovalent non-aromatic are condensed miscellaneous more ring groups, xenyl and terphenyl.

Term " Ph " as used herein can refer to phenyl；Term " Me " as used herein can be with nail base；As here The term " Et " used can refer to ethyl；Term " ter-Bu " or " Bu as used herein^t" tert-butyl group can be referred to；As made here Term " OMe " can be with nail epoxide.

Term " xenyl " as used herein refers to " phenyl that substitution has phenyl ".In other words, " xenyl " is with C₆- C₆₀Substituted phenyl of the aryl as substituent.

Term " terphenyl " as used herein refers to " phenyl that substitution has xenyl ".In other words, " terphenyl " is There is C with substitution₆-C₆₀The C of aryl₆-C₆₀Substituted phenyl of the aryl as substituent.

Unless otherwise defined, otherwise * and * ' used herein refer both to the bound site with the adjacent atom in corresponding.

Following example and comparative examples are provided, with the feature of one or more embodiments of protrusion, it will be understood that , example and comparative examples are not construed as limiting the scope of embodiment, and comparative examples are also not construed as in embodiment Outside scope.In addition, it will be understood that embodiment is not limited to the detail described in example and comparative examples.

Hereinafter, will be described in detail with reference to synthesis example and example according to the compound of embodiment and according to embodiment Organic luminescent device." using B to refer to instead of A " uses the B of identical molar equivalent to replace for the statement used during description synthesis example A。

[example]

[synthesis example]

[synthesis example 1：The synthesis of compound 1]

Intermediate product 1-1 synthesis

By 1.85g (10mmol) 2- bromobenzaldehydes, 2.22g (10mmol) 4- bromonaphthalene -1- amine, 0.23g The Pd of (0.25mmol)₂dba₃, 0.28g (0.5mmol) double (diphenylphosphino) ferrocene (dppf) of 1,1'- and 2.76g The K of (20mmol)₂CO₃It is dissolved in 250mL toluene, and is stirred 24 hours at a temperature of 80 DEG C.The reaction solution that will be obtained Room temperature is cooled to, and is filtered by diatomite (Celite).It is dried under reduced pressure obtained filtrate (filtrate).It is added to 2.67g (20mmol) AlCl₃, and weight molten (remelt) is performed in 300mL toluene.By temperature of the resulting solution at 80 DEG C Lower stirring 24 hours.Obtained reaction solution is cooled to room temperature.Then, extracted by using 60mL water and 60mL diethyl ether Take organic layer three times.The organic layer being dried to obtain by using magnesium sulfate, and evaporate solvent.By silica gel column chromatography separation simultaneously Obtained residue is purified, so as to complete 1.53g intermediate product 1-1 (50%) preparation.Intermediate product is determined by LC-MS 1-1。

C₁₇H₁₁NBr：M+1 308.17

The synthesis of compound 1

By 3.07g (10mmol) intermediate product 1-1,4.3g (10mmol) 4,4,5,5- tetramethyls -2- (10- (naphthalene - 1- yls) anthracene -9- bases) -1,3,2- dioxaborolanes, 0.58g (0.5mmol) Pd (PPh₃)₄With 4.15g (30.0mmol) K₂CO₃It is dissolved in tetrahydrofuran (THF) and H₂O(2:1 volume ratio) 180mL mixed solutions in, then at a temperature of 80 DEG C Stirring 16 hours.Obtained reaction solution is cooled to room temperature.Then, extracted by using 60mL water and 60mL diethyl ether Organic layer is three times.The organic layer being dried to obtain by using magnesium sulfate, and evaporate solvent.Separated by silica gel column chromatography and pure Change obtained residue, so as to complete the preparation of 3.7g compound 1 (70%).By LC-MS and¹H NMR determine compound 1。

C₄₁H₂₅N：M+1 531.65

[synthesis example 2：The synthesis of compound 19]

The synthesis of compound 19

Except using 9,9- dimethyl -7- (4- (4,4,5,5- tetramethyl -1,3,2- dioxaborolanes -2- bases) benzene Base) -9H- fluorenes -2- formonitrile HCNs replace synthesis compound 1 when 4,4,5,5- tetramethyls -2- (10- (naphthalene -1- bases) anthracene -9- bases) -1, Outside 3,2- dioxaborolanes, identical mode synthesizes 3.6g compound in a manner of in the synthesis with compound 1 19 (65%).By LC-MS and¹H NMR determine compound 19.

C₃₉H₂₆N₂：M+1 522.64

[synthesis example 3：The synthesis of compound 32]

The synthesis of compound 32

By 3.07g (10mmol) intermediate product 1-1,3.9g (10mmol) diphenyl (3- (4,4,5,5- tetramethyls- 1,3,2- dioxaborolanes -2- bases) phenyl) phosphine, 0.58g (0.5mmol) Pd (PPh₃)₄With 4.15g's (30.0mmol) K₂CO₃It is dissolved in THF and H₂O(2:1 volume ratio) 180mL mixed solutions in, then stirred 16 hours at a temperature of 80 DEG C. Obtained reaction solution is cooled to room temperature.Then, organic layer is extracted three times by using 60mL water and 60mL diethyl ether. The organic layer being dried to obtain by using magnesium sulfate, and evaporate solvent.Obtained residue is dissolved in 40mL dichloromethane In.4mL hydrogen peroxide is added in obtained solution, and mixed solution is stirred at room temperature 20 hours.Then, Xiang Qitian Add 20mL water, and organic layer is extracted three times by using 20mL dichloromethane.Have by using what magnesium sulfate was dried to obtain Machine layer, and evaporate solvent.Separated by silica gel column chromatography and purify obtained residue, so as to complete 2.52g compound The preparation of 32 (50%).By LC-MS and¹H NMR determine compound 32.

C₃₅H₂₄NOP：M+1 505.55

[synthesis example 4：The synthesis of compound 42]

The synthesis of compound 42

Except using diphenyl (4- (10- (4,4,5,5- tetramethyl -1,3,2- dioxaborolanes -2- bases) anthracene -9- Base) phenyl) phosphine oxide replace synthesis compound 1 when 4,4,5,5- tetramethyls -2- (10- (naphthalene -1- bases) anthracene -9- bases) -1,3, Outside 2- dioxaborolanes, identical mode synthesizes 4.4g compound 42 in a manner of in the synthesis with compound 1 (65%).By LC-MS and¹H NMR determine compound 42.

C₄₉H₃₂NOP：M+1 681.78

[synthesis example 5：The synthesis of compound 43]

The synthesis of compound 43

Except using diphenyl (6- (4,4,5,5- tetramethyl -1,3,2- dioxaborolanes -2- bases) naphthalene -2- bases) phosphine Instead of synthesizing the diphenyl (3- (4,4,5,5- tetramethyl -1,3,2- dioxaborolanes -2- bases) phenyl) during compound 32 Outside phosphine, identical mode synthesizes 2.2g compound 43 (50%) in a manner of in the synthesis with compound 32.Pass through LC- MS and¹H NMR determine compound 43.

C₃₉H₂₆NOP：M+1 555.64

[synthesis example 6：The synthesis of compound 46]

The synthesis of compound 46

Except using diphenyl (6- (4,4,5,5- tetramethyl -1,3,2- dioxaborolanes -2- bases) -4,5a1- two Hydrogen pyrene -1- bases) phosphine replace synthesis compound 32 when the diphenyl (3- (boron of 4,4,5,5- tetramethyl -1,3,2- dioxanes penta Alkane -2- bases) phenyl) outside phosphine, identical mode synthesizes 3.15g compound 46 in a manner of in the synthesis with compound 32 (50%).By LC-MS and¹H NMR determine compound 46.

C₄₅H₂₈NOP：M+1 629.68

[synthesis example 7：The synthesis of compound 49]

The synthesis of compound 49

Except using 9,9- dimethyl -2- (4,4,5,5- tetramethyl -1,3,2- dioxaborolanes -2- bases) -4a, 9- Dihydro -4H- fluorenes -7- bases) diphenylphosphine replace synthesis compound 32 when diphenyl (3- (4,4,5,5- tetramethyls -1,3,2- two Oxa- ring pentaborane -2- bases) phenyl) outside phosphine, identical mode synthesizes 2.5g in a manner of in the synthesis with compound 32 Compound 49 (40%).By LC-MS and¹H NMR determine compound 49.C₄₄H₃₂NOP：M+1 621.70

[synthesis example 8：The synthesis of compound 67]

The synthesis of compound 67

Except using 9,9- diphenyl -2- (4,4,5,5- tetramethyl -1,3,2- dioxaborolanes -2- bases) -4a, 9- Dihydro -4H- fluorenes -7- formonitrile HCNs replace the 4,4,5,5- tetramethyls -2- (10- (naphthalene -1- bases) anthracene -9- bases) -1 during synthesis compound 1, Outside 3,2- dioxaborolanes, identical mode synthesizes 4.0g compound in a manner of in the synthesis with compound 1 67 (70%).By LC-MS and¹H NMR determine compound 67.

C₄₃H₂₆N₂：M+1 570.70

[synthesis example 9：The synthesis of compound 68]

The synthesis of compound 68

Except using the boron of 2- (9,10- bis- (naphthalene -2- bases) anthracene -2- bases) -4,4,5,5- tetramethyl -1,3,2- dioxanes penta Alkane replaces 4,4,5,5- tetramethyls -2- (10- (naphthalene -1- bases) anthracene -9- bases) -1,3,2- dioxanes penta during synthesis compound 1 Outside borine, identical mode synthesizes 3.6g compound 68 (55%) in a manner of in the synthesis with compound 1.Pass through LC-MS and¹H NMR determine compound 68.

C₅₁H₃₁N：M+1 657.81

[synthesis example 10：The synthesis of compound 73]

Intermediate product 73-1 synthesis

By 2.9g (10mmol) Isosorbide-5-Nitrae-two bromo- 2,3,5,6- durols are dissolved in 200mL tetrahydrofuran (THF), 4mL (in hexane, 2.5M) n-BuLi is added at a temperature of -78 DEG C.After one hour, dissolving is slowly added dropwise There is the 40mL of 2.70g (10mmol) fluorine trimethylphenyl borine THF, and be stirred solution 3 hours.For reaction After temperature is warmed to room temperature, water is added to, and washing process is performed three times to it by using ethyl acetate (30mL).Pass through Use magnesium sulfate (MgSO₄) ethyl acetate layer of thus obtained washing is dried, and be dried under reduced pressure, then, pass through silicagel column color Spectrum is separated and purified, so as to obtain 2.95g intermediate product 73-2 (yields：64%).Intermediate product 73- is determined by LC-MS 1。

C₂₈H₃₄BBr：M+1 461.3

Intermediate product 73-2 synthesis

By 4.61g (10mmol) intermediate product 73-1,2.54g (10mmol) double (pinacol conjunction) two boron, 0.35g Pd (the PPh of (0.5mmol)₃)₂Cl₂It is dissolved in 2.94g (30mmol) KOAc in 60mL toluene, then in 100 DEG C of temperature Lower stirring 16 hours.Obtained reaction solution is cooled to room temperature.Then, extracted by using 40mL water and 50mL ether Organic layer is three times.The organic layer being dried to obtain by using magnesium sulfate, and evaporate solvent.Separated by silica gel column chromatography and pure Change obtained residue, so as to obtain 4.38g intermediate product 73-2 (yields：70%).Intermediate product is determined by LC-MS 73-2。

C₃₄H₄₆B₂O₂：M+1 508.32

The synthesis of compound 73

By 5.08g (10mmol) intermediate product 73-2,3.08g (10mmol) intermediate product 1-1,0.58g Pd (the PPh of (0.5mmol)₃)₄With 4.15g (30.0mmol) K₂CO₃It is dissolved in THF/H₂O(2:1) in 180mL mixed solutions, Then stirred 16 hours at a temperature of 80 DEG C.Obtained reaction solution is cooled to room temperature.Then, by using 60mL water Organic layer is extracted with 60mL diethyl ether three times.The organic layer being dried to obtain by using magnesium sulfate, and evaporate solvent.Pass through Silica gel column chromatography separates and purifies obtained residue, so as to obtain the 4.8g (yield of compound 73：70%).Pass through LC-MS With¹H NMR determine compound 73.

C₅₁H₄₈BN：M+1 685.74

[table 1]

[example 1]

By that will deposit thereon respectivelyITO/Ag/ITO ito glass substrate cut into 50mm × 50mm × 0.5mm size, it is cleaned by ultrasonic ito glass substrate (anode) each 5 minutes using isopropanol and pure water, so Afterwards, ito glass substrate (anode) is irradiated 30 minutes exposed to UV, and is exposed to ozone to clean ito glass substrate Prepare anode.Then, ito glass substrate (anode) is loaded into vacuum deposition apparatus.

With 98 in ito glass substrate (anode):2 weight is than being co-deposited N- ([1,1'- biphenyl] -4- bases)-N- (4- (9- phenyl -9H- carbazole -3- bases) phenyl) -9,9- dimethyl -9H- fluorenes -2- amine (compound 301) and F4-TCNQ, to form tool HaveThickness hole injection layer.Compound of the vacuum moulding machine as hole transport compound on hole injection layer 301, have to be formedThickness the first hole transmission layer.Vacuum moulding machine N, N- bis- on the first hole transmission layer ([1,1'- biphenyl] -4- bases) -4'- (9H- carbazole -9- bases)-[1,1'- xenyl] -4- amine (compound A), have to be formedThickness the second hole transmission layer.

With 98 on the second hole transmission layer:2 weight is than being co-deposited bis--naphthalenes of 9,10- -2- as blue-fluorescence main body Base-anthracene (ADN) and the N as blue-fluorescence dopant, N, N', N'- tetraphenyl-pyrene -1,6- diamines (TPD), have to be formedThickness emission layer.

Then, on the emitter with 5:5 weight has than being co-deposited compound 1 and LiQ to be formedThickness Electron transfer layer, be deposited as the LiF of alkali halide on the electron transport layer, have to be formedThickness electricity Sub- implanted layer, with 90 on electron injecting layer:10 weight has than vacuum moulding machine Mg and Ag to be formedThickness Cathode electrode, so as to complete the manufacture of organic luminescent device.

[example 2 to example 10 and comparative examples 1 to comparative examples 4]

When forming electron transfer layer respectively using table 1 in addition to the compound that shows replaces compound 1, with showing Mode identical mode in example 1 manufactures example 2 to example 10 and comparative examples 1 to the organic luminescent device of comparative examples 4.

[evaluation example 1]

Evaluate 10mA/cm²Current density under example 1 manufactured into comparative examples 4 to example 10 and comparative examples 1 Driving voltage, efficiency and the color of organic luminescent device are marked.Life-span, (T97) referred in 1.0mA/cm²Current density under until bright Degree is reduced to 97% period passed of original intensity.Its result is shown in table 2.

[table 2]

With reference to table 2, it was demonstrated that, with driving voltage of the comparative examples 1 to the organic luminescent device of comparative examples 4, efficiency Compared with the life-span, the organic luminescent device of example 1 to example 10 has low driving voltage, high efficiency and long-life.

Low driving can be had according to the organic luminescent device of one or more embodiments, including the heterocyclic compound Voltage, high efficiency and long-life.

It should be understood that the embodiments described herein should be to be considered merely as descriptive implication, rather than for limitation Purpose.The description of feature or aspect in each embodiment should generally be considered to be useful for other similar spies in other embodiments Sign or aspect.

There has been disclosed exemplary embodiment, concrete term despite the use of, but only with general and descriptive Implication and nonrestrictive purpose use and explained these terms.It is when in some cases, such as submission the application It will be apparent that, unless expressly stated otherwise, otherwise described in conjunction with specific embodiments for those of ordinary skill in the art only Feature, characteristic and/or element can be used alone, or can with combine other embodiments description feature, characteristic and/or element It is applied in combination.Therefore, it will be appreciated by those skilled in the art that the essence of the invention illustrated in not departing from such as claims In the case of refreshing and scope, various changes can be carried out in form and details.

Claims

1. a kind of heterocyclic compound, the heterocyclic compound is represented by formula 1：

*-(L₁₁)_a11-(R₁₂)_b12,

Wherein, in formula 1,

R₅For the group represented by formula 2,

R₁To R₄And R₆To R₁₁Independently selected from：

The group that is represented by formula 2, hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, substitution or Unsubstituted C₁-C₆₀Alkyl, substituted or unsubstituted C₂-C₆₀Alkenyl, substituted or unsubstituted C₂-C₆₀Alkynyl, substitution do not take The C in generation₁-C₆₀Alkoxy, substituted or unsubstituted C₃-C₁₀Cycloalkyl, substituted or unsubstituted C₁-C₁₀Heterocyclylalkyl, substitution or Unsubstituted C₃-C₁₀Cycloalkenyl group, substituted or unsubstituted C₁-C₁₀Heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Aryl, substitution Or unsubstituted C₆-C₆₀Aryloxy group, substituted or unsubstituted C₆-C₆₀Arylthio, substituted or unsubstituted C₁-C₆₀Heteroaryl, take Generation or unsubstituted monovalent non-aromatic condensation polycyclic base, substituted or unsubstituted monovalent non-aromatic are condensed miscellaneous more ring groups ,-N (Q₁) (Q₂)、-Si(Q₁)(Q₂)(Q₃) and-B (Q₁)(Q₂),

In formula 2,

L₁₁Selected from substituted or unsubstituted C₃-C₁₀Cycloalkylidene, substituted or unsubstituted C₁-C₁₀Sub- Heterocyclylalkyl, substitution or Unsubstituted C₃-C₁₀Sub- cycloalkenyl group, substituted or unsubstituted C₁-C₁₀Sub- heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Sub- virtue Base, substituted or unsubstituted C₁-C₆₀The non-aromatic condensation polycyclic base of inferior heteroaryl, substituted or unsubstituted divalence, substitution do not take The miscellaneous more ring groups of the non-aromatic condensation of divalence in generation, *-P (=O) (Q₄)-* ', *-P (=S) (Q₄)-* ', *-S (=O)-* ' and *-S (= O)₂- * ',

A11 be selected from 0 to 3 integer, wherein, when a11 be two or bigger when, two or more L₁₁It is mutually the same or each other Difference,

R₁₂Selected from substituted or unsubstituted C₃-C₁₀Cycloalkyl, substituted or unsubstituted C₁-C₁₀Heterocyclylalkyl, substitution do not take The C in generation₃-C₁₀Cycloalkenyl group, substituted or unsubstituted C₁-C₁₀Heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Aryl, substitution or not Substituted C₆-C₆₀Aryloxy group, substituted or unsubstituted C₆-C₆₀Arylthio, substituted or unsubstituted C₁-C₆₀Heteroaryl, substitution or Unsubstituted monovalent non-aromatic condensation polycyclic base, substituted or unsubstituted monovalent non-aromatic are condensed miscellaneous more ring groups ,-Si (Q₄)(Q₅) (Q₆)、-N(Q₄)(Q₅)、-B(Q₄)(Q₅) ,-C (=O) (Q₄) ,-P (=O) (Q₄)(Q₅) ,-P (=S) (Q₄)(Q₅) ,-S (=O) (Q₄) and-S (=O)₂(Q₄),

B12 be selected from 1 to 3 integer, wherein, when b12 be two or bigger when, two or more R₁₂It is mutually the same or each other Difference, and

From substituted C₃-C₁₀Cycloalkylidene, the C of substitution₁-C₁₀Sub- Heterocyclylalkyl, the C of substitution₃-C₁₀Sub- cycloalkenyl group, the C of substitution₁- C₁₀Sub- heterocycloalkenyl, the C of substitution₆-C₆₀Arlydene, the C of substitution₁-C₆₀Inferior heteroaryl, the non-aromatic condensation polycyclic of divalence of substitution The miscellaneous more ring groups of the non-aromatic condensation of base, the divalence of substitution, the C of substitution₁-C₆₀Alkyl, the C of substitution₂-C₆₀Alkenyl, the C of substitution₂-C₆₀Alkynes Base, the C of substitution₁-C₆₀Alkoxy, the C of substitution₃-C₁₀Cycloalkyl, the C of substitution₁-C₁₀Heterocyclylalkyl, the C of substitution₃-C₁₀Cycloalkenyl group, Substituted C₁-C₁₀Heterocycloalkenyl, the C of substitution₆-C₆₀Aryl, the C of substitution₆-C₆₀Aryloxy group, the C of substitution₆-C₆₀Arylthio, substitution C₁-C₆₀Heteroaryl, the monovalent non-aromatic condensation polycyclic base of substitution and substituted monovalent non-aromatic are condensed the substitution of miscellaneous more ring groups At least one substituent selected in base is selected from：

Deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, substituted or unsubstituted C₁-C₆₀Alkyl, take Generation or unsubstituted C₂-C₆₀Alkenyl, substituted or unsubstituted C₂-C₆₀Alkynyl and substituted or unsubstituted C₁-C₆₀Alkoxy；

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₃-C₁₀Cycloalkyl, C₁-C₁₀Heterocyclylalkyl, C₃-C₁₀Cycloalkenyl group, C₁-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl, C₆-C₆₀Aryloxy group, C₆-C₆₀Arylthio, C₁- C₆₀Heteroaryl, monovalent non-aromatic condensation polycyclic base, monovalent non-aromatic are condensed miscellaneous more ring groups ,-Si (Q₁₁)(Q₁₂)(Q₁₃)、-N(Q₁₁) (Q₁₂)、-B(Q₁₁)(Q₁₂) ,-C (=O) (Q₁₁) ,-S (=O)₂(Q₁₁) and-P (=O) (Q₁₁)(Q₁₂) at least one of C₁- C₆₀Alkyl, C₂-C₆₀Alkenyl, C₂-C₆₀Alkynyl and C₁-C₆₀Alkoxy；

C₃-C₁₀Cycloalkyl, C₁-C₁₀Heterocyclylalkyl, C₃-C₁₀Cycloalkenyl group, C₁-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl, C₆-C₆₀Fragrant oxygen Base, C₆-C₆₀Arylthio, C₁-C₆₀Heteroaryl, monovalent non-aromatic condensation polycyclic base and monovalent non-aromatic are condensed miscellaneous more ring groups；

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₆₀Alkyl, C₂- C₆₀Alkenyl, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy, C₃-C₁₀Cycloalkyl, C₁-C₁₀Heterocyclylalkyl, C₃-C₁₀Cycloalkenyl group, C₁-C₁₀Heterocycle Alkenyl, C₆-C₆₀Aryl, C₆-C₆₀Aryloxy group, C₆-C₆₀Arylthio, C₁-C₆₀Heteroaryl, monovalent non-aromatic condensation polycyclic base, unit price It is non-aromatic to be condensed miscellaneous more ring groups ,-Si (Q₂₁)(Q₂₂)(Q₂₃)、-N(Q₂₁)(Q₂₂)、-B(Q₂₁)(Q₂₂) ,-C (=O) (Q₂₁) ,-S (= O)₂(Q₂₁) and-P (=O) (Q₂₁)(Q₂₂) at least one of C₃-C₁₀Cycloalkyl, C₁-C₁₀Heterocyclylalkyl, C₃-C₁₀Cycloalkenyl group, C₁-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl, C₆-C₆₀Aryloxy group, C₆-C₆₀Arylthio, C₁-C₆₀Heteroaryl, monovalent non-aromatic condensation are more Ring group and monovalent non-aromatic are condensed miscellaneous more ring groups；And

-Si(Q₃₁)(Q₃₂)(Q₃₃)、-N(Q₃₁)(Q₃₂)、-B(Q₃₁)(Q₃₂) ,-C (=O) (Q₃₁) ,-S (=O)₂(Q₃₁) and-P (=O) (Q₃₁)(Q₃₂),

Q₁To Q₆、Q₁₁To Q₁₃、Q₂₁To Q₂₃And Q₃₁To Q₃₃Independently selected from hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, Nitro, amidino groups, diazanyl, hydrazone group, C₁-C₆₀Alkyl, C₂-C₆₀Alkenyl, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy, C₃-C₁₀Cycloalkyl, C₁- C₁₀Heterocyclylalkyl, C₃-C₁₀Cycloalkenyl group, C₁-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl, C₁-C₆₀Heteroaryl, monovalent non-aromatic condensation polycyclic Base, monovalent non-aromatic are condensed miscellaneous more ring groups, xenyl and terphenyl, and

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group and C₁-C₆₀In alkyl The C of at least one₃-C₁₀Cycloalkyl, C₁-C₁₀Heterocyclylalkyl, C₃-C₁₀Cycloalkenyl group, C₁-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl, C₁- C₆₀Heteroaryl, monovalent non-aromatic condensation polycyclic base, monovalent non-aromatic are condensed miscellaneous more ring groups, xenyl and terphenyl；And

* represented with * ' and the bound site of adjacent atom.

2. heterocyclic compound according to claim 1, wherein,

L₁₁It is selected from：

Phenylene, sub- pentalene base, sub-indenyl, naphthylene, sub- camomile ring group, sub- indacene base, sub- acenaphthenyl, fluorenylidene, The sub- fluorenyl of spiral shell two, sub- spiral shell benzfluorene-fluorenyl, sub- benzo fluorenyl, sub- dibenzo fluorenyl, that alkenyl of Asia and Africa, phenanthrylene, anthrylene, Sub- fluoranthene base, sub- benzo [9,10] phenanthryl, sub- pyrenyl, AsiaBase, subunit, sub- pentacene base, sub- pyrrole radicals, sub- thienyl, Furylidene, sub- thiophene cough up base, sub- imidazole radicals, sub- pyrazolyl, sub- thiazolyl, sub- isothiazolyl, Ya oxazolyls, Ya isoxazolyls, Sub- pyridine radicals, sub- pyrazinyl, sub- pyrimidine radicals, sub- pyridazinyl, sub- indyl, sub- isoindolyl, sub- indazolyl, sub- purine radicals, Asia Quinolyl, sub- isoquinolyl, sub- benzoquinoline base, sub- benzisoquinoline base, sub- phthalazinyl, sub- naphthyridines base, sub- quinoxalinyl, Asia Quinazolyl, sub- cinnolines base, sub- phenanthridinyl, sub- acridinyl, sub- phenanthroline, sub- phenazinyl, sub- benzimidazolyl, sub- benzo furan Mutter base, sub- benzothienyl, sub- benzo thiophene coughs up base, sub- benzothiazolyl, sub- different benzothiazolyl, sub- benzoxazolyl, sub- different Benzoxazolyl, sub- triazolyl, sub- tetrazole radical, Ya oxadiazolyls, sub- triazine radical, sub- carbazyl, sub- dibenzofuran group, Asia two Benzothienyl, sub- dibenzo thiophene cough up base, sub- benzo carbazole base, sub- naphtho- benzofuranyl, sub- naphtho- benzothienyl, sub- naphthalene And benzo thiophene coughs up base, sub- dibenzo-carbazole base, sub- dinaphtho furyl, sub- dinaphtho thienyl, sub- dinaphtho thiophene and coughs up base, sub- thiophene Di azoly, sub- imidazopyridyl, sub- imidazopyrimidine base, Ya oxazoles and pyridine radicals, sub- thiazolopyridinyl, sub- benzo naphthyridines Base, sub- azepine fluorenyl, the fluorenyl of sub- azaspiro two, sub- azepine carbazyl, sub- azepine dibenzofuran group, sub- azepine dibenzothiophenes Base, sub- azepine dibenzo thiophene cough up base, sub- indeno-pyrrole base, sub- indoles and pyrrole radicals, sub- indeno carbazyl and sub- indolocarbazole Base；And

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkyl, C₁- C₂₀Alkoxy, C₃-C₁₀Cycloalkyl, C₁-C₁₀Heterocyclylalkyl, C₃-C₁₀Cycloalkenyl group, C₁-C₁₀Heterocycloalkenyl, C₆-C₂₀Aryl, C₁-C₂₀ Heteroaryl, monovalent non-aromatic condensation polycyclic base, monovalent non-aromatic are condensed miscellaneous more ring groups, aminomethyl phenyl, xenyl and-Si (Q₃₁) (Q₃₂)(Q₃₃) at least one of phenylene, sub- pentalene base, sub-indenyl, naphthylene, sub- camomile ring group, Asia draw and reach Save base, sub- acenaphthenyl, fluorenylidene, the fluorenyl of sub- spiral shell two, sub- spiral shell benzfluorene-fluorenyl, sub- benzo fluorenyl, sub- dibenzo fluorenyl, Asia and Africa that Alkenyl, phenanthrylene, anthrylene, sub- fluoranthene base, sub- benzo [9,10] phenanthryl, sub- pyrenyl, AsiaBase, subunit, sub- pentacene base, Sub- pyrrole radicals, sub- thienyl, furylidene, sub- thiophene cough up base, sub- imidazole radicals, sub- pyrazolyl, sub- thiazolyl, sub- isothiazolyl, Asia Oxazolyl, Ya isoxazolyls, sub- pyridine radicals, sub- pyrazinyl, sub- pyrimidine radicals, sub- pyridazinyl, sub- indyl, sub- isoindolyl, Asia Indazolyl, sub- purine radicals, sub- quinolyl, sub- isoquinolyl, sub- benzoquinoline base, sub- benzisoquinoline base, sub- phthalazinyl, sub- naphthalene Piperidinyl, sub- quinoxalinyl, sub- quinazolyl, sub- cinnolines base, sub- phenanthridinyl, sub- acridinyl, sub- phenanthroline, sub- phenazinyl, Asia Benzimidazolyl, sub- benzofuranyl, sub- benzothienyl, sub- benzo thiophene cough up base, sub- benzothiazolyl, sub- different benzothiazole Base, sub- benzoxazolyl, sub- Yi benzoxazolyls, sub- triazolyl, sub- tetrazole radical, Ya oxadiazolyls, sub- triazine radical, sub- carbazole Base, sub- dibenzofuran group, sub- dibenzothiophenes base, sub- dibenzo thiophene cough up base, sub- benzo carbazole base, sub- naphtho- benzofuran Base, sub- naphtho- benzothienyl, sub- naphtho- benzo thiophene cough up base, sub- dibenzo-carbazole base, sub- dinaphtho furyl, sub- dinaphtho thiophene Fen base, sub- dinaphtho thiophene cough up base, sub- thiadiazolyl group, sub- imidazopyridyl, sub- imidazopyrimidine base, Ya oxazoles and pyridine radicals, Sub- thiazolopyridinyl, sub- benzo naphthyridines base, sub- azepine fluorenyl, the fluorenyl of sub- azaspiro two, sub- azepine carbazyl, sub- azepine hexichol And furyl, sub- azepine dibenzothiophenes base, sub- azepine dibenzo thiophene cough up base, sub- indeno-pyrrole base, sub- indoles and pyrrole radicals, Asia Indeno carbazyl and sub- indolocarbazole base；And

*-P (=O) (Q₄)-* ', *-P (=S) (Q₄)-* ', *-S (=O)-* ' and *-S (=O)₂- * ',

Wherein, Q₄And Q₃₁To Q₃₃Independently selected from：

C₁-C₁₀Alkyl, C₁-C₁₀Alkoxy, phenyl, xenyl, terphenyl, naphthyl, pyridine radicals, pyrimidine radicals, pyrazinyl, quinoline Base, isoquinolyl, quinoxalinyl and quinazolyl；And

Substitution has selected from C₁-C₁₀Alkyl, C₁-C₁₀Phenyl, xenyl, the terphenyl of at least one of alkoxy and phenyl Base, naphthyl, pyridine radicals, pyrimidine radicals, pyrazinyl, quinolyl, isoquinolyl, quinoxalinyl and quinazolyl.

3. heterocyclic compound according to claim 1, wherein,

L₁₁Selected from *-P (=O) (Q₄)-* ', *-P (=S) (Q₄)-* ', *-S (=O)-* ', *-S (=O)₂- * ' and by formula 3-1 The group represented to formula 3-47：

Wherein, in formula 3-1 into formula 3-47,

Y₁For O, S, C (Z₃)(Z₄)、N(Z₅) or Si (Z₆)(Z₇),

Z₁To Z₇Independently selected from：

Hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkyl, C₁-C₂₀Alkoxy, Cyclopenta, cyclohexyl, suberyl, cyclopentenyl, cyclohexenyl group, phenyl, xenyl, terphenyl, pentalene base, indenes Base, naphthyl, camomile ring group, indacene base, acenaphthenyl, fluorenyl, the fluorenyl of spiral shell two, spiral shell benzfluorene-fluorenyl, benzo fluorenyl, dibenzo fluorenes Base, that non-alkenyl, phenanthryl, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, base, pentacene base, pyrrole radicals, thiophene Fen base, furyl, thiophene cough up base, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyls, pyridine radicals, pyrazine It is base, pyrimidine radicals, pyridazinyl, indyl, isoindolyl, indazolyl, purine radicals, quinolyl, isoquinolyl, benzoquinoline base, different Quinolyl, phthalazinyl, naphthyridines base, quinoxalinyl, Benzoquinoxalines base, quinazolyl, Benzoquinazole base, cinnolines base, phenanthridines Base, acridinyl, phenanthroline, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzo thiophene cough up base, benzo thiophene Oxazolyl, different benzothiazolyl, benzoxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, oxadiazolyls, triazine radical, carbazole Base, dibenzofuran group, dibenzothiophenes base, dibenzo thiophene cough up base, benzo carbazole base, naphtho- benzofuranyl, naphtho- benzo Thienyl, naphtho- benzo thiophene cough up base, dibenzo-carbazole base, dinaphtho furyl, dinaphtho thienyl, dinaphtho thiophene and cough up base, thiophene Di azoly, imidazopyridyl, imidazopyrimidine base, oxazoles and pyridine radicals, thiazolopyridinyl, benzo naphthyridines base, azepine fluorenes Base, the fluorenyl of azaspiro two, azepine carbazyl, azepine dibenzofuran group, azepine dibenzothiophenes base, azepine dibenzo thiophene are coughed up Base, indeno-pyrrole base, indoles and pyrrole radicals, indeno carbazyl and indolocarbazole base,

Q₄Selected from hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₆₀Alkyl, phenyl, Xenyl and terphenyl；And

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group and C₁-C₆₀In alkyl The phenyl of at least one, xenyl and terphenyl,

D2 be selected from 1 and 2 integer,

D3 be selected from 1 to 3 integer,

D4 be selected from 1 to 4 integer,

D5 be selected from 1 to 5 integer,

D6 be selected from 1 to 6 integer,

D8 be selected from 1 to 8 integer, and

* represented with * ' and the bound site of adjacent atom.

4. heterocyclic compound according to claim 3, wherein,

L₁₁Selected from *-P (=O) (Q₄)-* and by formula 3-1, formula 3-2, formula 3-3, formula 3-6, formula 3-12, formula 3-14, formula 3-31 The group represented with formula 3-47, and

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group and C₁-C₆₀In alkyl The phenyl of at least one, xenyl and terphenyl.

5. heterocyclic compound according to claim 1, wherein,

L₁₁Selected from the group represented by formula 4-1 to formula 4-30：

6. heterocyclic compound according to claim 1, wherein,

A11 is 0,1 or 2.

7. heterocyclic compound according to claim 1, wherein,

R₁₂It is selected from：

It is phenyl, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, glimmering Anthryl, benzo [9,10] phenanthryl, pyrenyl,Base, base, pentaphene base, hexacene base, pentacene base, thienyl, furyl, click Oxazolyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole Base, dibenzo-carbazole base, dibenzo thiophene cough up base, pyridine radicals, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, Yi Evil Oxazolyl, thiadiazolyl group, oxadiazolyls, pyrazinyl, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinolyl, benzoquinoline Base, phthalazinyl, naphthyridines base, quinoxalinyl, quinazolyl, cinnolines base, phenanthridinyl, acridinyl, benzacridine base, phenanthroline, Phenazinyl, benzimidazolyl, different benzothiazolyl, benzoxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, imidazo pyrrole Piperidinyl, imidazopyrimidine base and azepine carbazyl；

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkyl, C₁- C₂₀Alkoxy, phenyl, xenyl, terphenyl, naphthyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthracene Base, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, base, pentaphene base, hexacene base, pentacene base, thienyl, furans Base, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophenes base, benzene And carbazyl, dibenzo-carbazole base, dibenzo thiophene cough up base, pyridine radicals, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazoles Base, isoxazolyls, thiadiazolyl group, oxadiazolyls, pyrazinyl, pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinolyl, benzene And quinolyl, phthalazinyl, naphthyridines base, quinoxalinyl, quinazolyl, cinnolines base, phenanthridinyl, acridinyl, benzacridine base, phenanthrene are coughed up Quinoline base, phenazinyl, benzimidazolyl, different benzothiazolyl, benzoxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, miaow The phenyl of azoles and at least one of pyridine radicals, imidazopyrimidine base and azepine carbazyl, xenyl, terphenyl, naphthyl, fluorenes Base, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, Base, pentaphene base, hexacene base, pentacene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, Benzothienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene cough up base, pyrrole Piperidinyl, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyls, thiadiazolyl group, oxadiazolyls, pyrazinyl, Pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, isoquinolyl, benzoquinoline base, phthalazinyl, naphthyridines base, quinoxalinyl, quinazoline Base, cinnolines base, phenanthridinyl, acridinyl, benzacridine base, phenanthroline, phenazinyl, benzimidazolyl, different benzothiazolyl, benzene Bing oxazolyls, Yi benzoxazolyls, triazolyl, tetrazole radical, imidazopyridyl, imidazopyrimidine base and azepine carbazyl；With And

-B(Q₄)(Q₅) ,-P (=O) (Q₄)(Q₅) ,-P (=S) (Q₄)(Q₅) ,-S (=O) (Q₄) and-S (=O)₂(Q₄),

Wherein, Q₄And Q₅Independently selected from：

8. heterocyclic compound according to claim 1, wherein,

R₁₂Selected from-B (Q₄)(Q₅) ,-P (=O) (Q₄)(Q₅) ,-P (=S) (Q₄)(Q₅) ,-S (=O) (Q₄) ,-S (=O)₂(Q₄) With the group represented by formula 5-1 to formula 5-90：

Wherein, in formula 5-1 into formula 5-90,

Y₃₁For O, S, C (Z₃₄)(Z₃₅)、N(Z₃₆) or Si (Z₃₇)(Z₃₈),

Z₃₁To Z₃₈Independently selected from hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁- C₂₀Alkyl, C₁-C₂₀Alkoxy, cyclopenta, cyclohexyl, suberyl, cyclopentenyl, cyclohexenyl group, phenyl, xenyl, terphenyl Base, pentalene base, indenyl, naphthyl, camomile ring group, indacene base, acenaphthenyl, fluorenyl, the fluorenyl of spiral shell two, spiral shell benzfluorene-fluorenyl, Benzo fluorenyl, dibenzo fluorenyl, that non-alkenyl, phenanthryl, anthryl, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, base, Pentacene base, pyrrole radicals, thienyl, furyl, thiophene cough up base, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl, oxazolyls, different Oxazolyl, pyridine radicals, pyrazinyl, pyrimidine radicals, pyridazinyl, indyl, isoindolyl, indazolyl, purine radicals, quinolyl, isoquinoline Quinoline base, benzoquinoline base, isoquinolyl, phthalazinyl, naphthyridines base, quinoxalinyl, Benzoquinoxalines base, quinazolyl, benzo quinoline Oxazoline base, cinnolines base, phenanthridinyl, acridinyl, phenanthroline, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, Benzo thiophene coughs up base, benzothiazolyl, different benzothiazolyl, benzoxazolyl, Yi benzoxazolyls, triazolyl, tetrazole radical, Evil bis- Oxazolyl, triazine radical, carbazyl, dibenzofuran group, dibenzothiophenes base, dibenzo thiophene cough up base, benzo carbazole base, naphtho- benzo Furyl, naphtho- benzothienyl, naphtho- benzo thiophene cough up base, dibenzo-carbazole base, dinaphtho furyl, dinaphtho thienyl, Dinaphtho thiophene coughs up base, thiadiazolyl group, imidazopyridyl, imidazopyrimidine base, oxazoles and pyridine radicals, thiazolopyridinyl, benzene And naphthyridines base, azepine fluorenyl, the fluorenyl of azaspiro two, azepine carbazyl, azepine dibenzofuran group, azepine dibenzothiophenes base, Azepine dibenzo thiophene coughs up base, indeno-pyrrole base, indoles and pyrrole radicals, indeno carbazyl and indolocarbazole base,

Q₄And Q₅Independently selected from C₁-C₁₀Alkyl, C₁-C₁₀Alkoxy, phenyl, xenyl, terphenyl, naphthyl, pyridine Base, pyrimidine radicals, pyrazinyl, quinolyl, isoquinolyl, quinoxalinyl and quinazolyl；And

Substitution has selected from C₁-C₁₀Alkyl, C₁-C₁₀Phenyl, xenyl, the terphenyl of at least one of alkoxy and phenyl Base, naphthyl, pyridine radicals, pyrimidine radicals, pyrazinyl, quinolyl, isoquinolyl, quinoxalinyl and quinazolyl,

E2 be selected from 1 and 2 integer,

E3 be selected from 1 to 3 integer,

E4 be selected from 1 to 4 integer,

E5 be selected from 1 to 5 integer,

E6 be selected from 1 to 6 integer,

E7 be selected from 1 to 7 integer,

E9 be selected from 1 to 9 integer, and

* the bound site with adjacent atom is represented.

9. heterocyclic compound according to claim 8, wherein,

R₁₂Selected from-B (Q₄)(Q₅) ,-P (=O) (Q₄)(Q₅) and by formula 5-1, formula 5-3, formula 5-4, formula 5-13 to formula 5-15 and The group that formula 5-21 represents to formula 5-23；And

Q₄And Q₅Independently selected from hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁- C₆₀Alkyl, phenyl, xenyl and terphenyl；And

10. heterocyclic compound according to claim 1, wherein,

R₁₂Selected from the group represented by formula 6-1 to formula 6-22：

11. heterocyclic compound according to claim 1, wherein,

B12 is 1 or 2.

12. heterocyclic compound according to claim 1, wherein,

R in formula 1₁To R₄And R₆To R₁₁Independently selected from：

The group represented by formula 2；

Hydrogen, deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkyl and C₁-C₂₀Alkoxy；

Phenyl, xenyl, terphenyl, pentalene base, indenyl, naphthyl, camomile ring group, heptalene base, indacene base, acenaphthene Base, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, that non-alkenyl, phenanthryl, anthryl, fluoranthene base, benzo [9,10] are luxuriant and rich with fragrance Base, pyrenyl,Base, aphthacene Ji, Pi base, base, pentaphene base, hexacene base, pentacene base, rubicene Ji, guans base, ovalene Base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuran group, two Benzothienyl, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene cough up base and pyridine radicals；

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkyl, C₁- C₂₀Alkoxy, cyclopenta, cyclohexyl, suberyl, cyclopentenyl, cyclohexenyl group, phenyl, xenyl, terphenyl, substitution have C₁-C₁₀The phenyl of alkyl, substitution have-F phenyl, pentalene base, indenyl, naphthyl, camomile ring group, heptalene base, draw and reach Save base, acenaphthenyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, that non-alkenyl, phenanthryl, anthryl, fluoranthene base, benzo [9, 10] phenanthryl, pyrenyl,Base, aphthacene Ji, Pi base, base, pentaphene base, hexacene base, pentacene base, rubicene Ji, guans base, Ovalene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofurans Base, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene cough up base, pyridine radicals ,-Si (Q₃₁)(Q₃₂)(Q₃₃) With-N (Q₃₁)(Q₃₂) at least one of phenyl, xenyl, terphenyl, pentalene base, indenyl, naphthyl, azulenes Base, heptalene base, indacene base, acenaphthenyl, fluorenyl, the fluorenyl of spiral shell two, benzo fluorenyl, dibenzo fluorenyl, that non-alkenyl, phenanthryl, anthracene Base, fluoranthene base, benzo [9,10] phenanthryl, pyrenyl,Base, aphthacene Ji, Pi base, base, pentaphene base, hexacene base, pentacene Base, rubicene Ji, guans base, ovalene base, thienyl, furyl, carbazyl, indyl, isoindolyl, benzofuranyl, benzo Thienyl, dibenzofuran group, dibenzothiophenes base, benzo carbazole base, dibenzo-carbazole base, dibenzo thiophene cough up base and pyridine Base；And

-Si(Q₁)(Q₂)(Q₃),

Wherein, Q₁To Q₃And Q₃₁To Q₃₃Independently selected from：

13. heterocyclic compound according to claim 12, wherein,

R in formula 1₁To R₄And R₆To R₁₁Independently selected from：

The group represented by formula 2；

Substitution has selected from least one of deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl and hydrazone group C₁-C₂₀Alkyl and C₁-C₂₀Alkoxy；

Substitution has selected from deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl, hydrazone group, C₁-C₂₀Alkyl, C₁- C₂₀At least one of alkoxy, cyclopenta, cyclohexyl, cyclopentenyl, cyclohexenyl group, phenyl, xenyl and terphenyl Cyclopenta, cyclohexyl, cyclopentenyl, cyclohexenyl group, phenyl, xenyl and terphenyl；And

-Si(Q₁)(Q₂)(Q₃),

Wherein, Q₁To Q₃Independently selected from C₁-C₂₀Alkyl, C₁-C₂₀Alkoxy, phenyl and naphthyl.

14. heterocyclic compound according to claim 1, wherein,

In formula 1,

R₁To R₄And R₆To R₁₁Independently selected from：

Substitution has selected from least one of deuterium ,-F ,-Cl ,-Br ,-I, hydroxyl, cyano group, nitro, amidino groups, diazanyl and hydrazone group C₁-C₂₀Alkyl and C₁-C₂₀Alkoxy；And

-Si(Q₁)(Q₂)(Q₃),

R₅For the group represented by formula 2,

Wherein, in formula 2,

L₁₁Selected from the group represented by formula 4-1 to formula 4-30,

A11 be selected from 0 to 2 integer,

R₁₂Selected from the group represented by formula 6-1 to formula 6-22,

B12 be selected from 1 and 2 integer, and

Q₁To Q₃Independently selected from C₁-C₂₀Alkyl, C₁-C₂₀Alkoxy, phenyl and naphthyl：

15. heterocyclic compound according to claim 1, wherein,

The heterocyclic compound is the compound to compound 87 selected from compound 1：

16. a kind of organic luminescent device, the organic luminescent device includes：

First electrode；

Second electrode, in face of the first electrode；And

Organic layer, it is arranged between the first electrode and the second electrode, and including emission layer,

Wherein, the organic layer includes heterocyclic compound according to claim 1.

17. organic luminescent device according to claim 16, wherein,

The first electrode is anode,

The second electrode is negative electrode, and

The organic layer includes：I) hole transporting zone, it is arranged between the first electrode and the emission layer, and including sky It is at least one in cave implanted layer, hole transmission layer, cushion and electronic barrier layer；And ii) electron transporting zone, it is arranged on Between the emission layer and the second electrode, and including in hole blocking layer, electron transfer layer and electron injecting layer at least One.

18. organic luminescent device according to claim 17, wherein,

What is selected from the emission layer and the electron transporting zone is at least one including the heterocyclic compound.

19. organic luminescent device according to claim 18, wherein,

The electron transporting zone includes electron transfer layer, and

The electron transfer layer includes the heterocyclic compound.

20. organic luminescent device according to claim 18, wherein,

The emission layer includes pyrene compound.