Phosphorescent host material and application thereof

文档序号：729192 发布日期：2021-04-20 浏览：33次中文

阅读说明：本技术 磷光主体材料及其应用 (Phosphorescent host material and application thereof ) 是由何锐锋吴灿洁杨曦宋晶尧于 2020-09-24 设计创作，主要内容包括：本发明公开了一种磷光主体材料,所述的磷光主体材料至少包含一种电子传输型(N型)主体材料H1及一种空穴传输型(P型)主体材料H2,其中H1和H2分别选自通式(1)和通式(2)所述的结构,按照本发明所述的磷光主体材料,运用于有机电子器件中时,能够有效地平衡电荷的传输和提高能量的利用率,从而有利于提高器件的效率和稳定性,为提高有机电子器件的效率和寿命提供一种行之有效的方案。(The invention discloses a phosphorescent main body material, which at least comprises an electron transport type (N type) main body material H1 and a hole transport type (P type) main body material H2, wherein H1 and H2 are respectively selected from structures shown in a general formula (1) and a general formula (2).)

1. A phosphorescent host material at least comprises an N-type host material H1 and a P-type host material H2, and is characterized in that: the N-type host material H1 is selected from a structure shown in a general formula (1):

wherein:

Ar¹selected from a substituted or unsubstituted aromatic group having 6 to 60 ring atoms or a substituted or unsubstituted heteroaromatic group having 6 to 60 ring atoms, and Ar¹Comprises at least one electron-deficient group;

Ar²、Ar³、Ar⁴each independently represents a substituted or unsubstituted aromatic group having 6 to 30 ring atoms or a substituted or unsubstituted heteroaromatic group having 6 to 30 ring atoms, N and Ar³May be Ar at the connecting position³On any one of the carbon atoms;

Z¹selected from the group consisting of CR₁R₂、SiR₁R₂、O、C＝NR₁、C＝CR₁、PR₁、P(＝O)R₁S, S ═ O or SO₂；

The P-type host material H2 is selected from a structure shown in a general formula (2):

wherein:

n is selected from 1,2,3 or 4;

Z²、Z³are independently selected from single bond and NR₄、CR₄R₅、SiR₄R₅、O、C＝O、C＝NR₄、C＝CR₄、PR₄、P(＝O)R₄S, S ═ O or SO₂；

R₁-R₅Independently at each occurrence, H, D, or a straight chain alkyl group having 1 to 20C atoms, or a straight chain alkyloxy group having 1 to 20C atoms, or a straight chain thioalkoxy group having 1 to 20C atoms, or a branched or cyclic alkyl group having 3 to 20C atomsAlkoxy, or branched or cyclic thioalkoxy having 3 to 20C atoms, or silyl, or keto having 1 to 20C atoms, or alkoxycarbonyl having 2 to 20C atoms, or aryloxycarbonyl having 7 to 20C atoms, or cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, CF₃Cl, Br, F, I, or a crosslinkable group, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems.

2. A phosphorescent host material according to claim 1, wherein: min (LUMO (H1) -HOMO (H2), LUMO (H2) -HOMO (H1)) < min (E1) ≦ min_T(H1),E_T(H2))+0.1eV；

Wherein: LUMO (H1) represents the lowest unoccupied orbital level of H1, HOMO (H1) represents the highest occupied orbital level of H1, E_T(H1) Represents the triplet energy level of H1; LUMO (H2) represents the lowest unoccupied orbital level of H2, HOMO (H2) represents the highest occupied orbital level of H2, E_T(H2) Represents the triplet energy level of H2.

3. A phosphorescent host material according to claim 1, wherein: ar (Ar)¹At least comprises one electron-deficient group, wherein the electron-deficient group is selected from F, a cyano group or one or more of the following groups:

wherein:

n1 represents any integer of 1 to 3;

each occurrence of X is independently selected from CR₆Or N, and at least one is N;

y is selected from NR₇、CR₇R₈、SiR₇R₈、O、S、S＝O、S(＝O)₂；

M¹、M²、M³Each independently represents NR₇、CR₇R₈、SiR₇R₈、O、C＝CR₇R₈、PR₇、P(＝O)R₇、S、S＝O、S(＝O)₂Or none;

R₆-R₈independently at each occurrence, H, D, or a straight chain alkyl group having 1 to 20C atoms, or a straight chain alkyloxy group having 1 to 20C atoms, or a straight chain thioalkoxy group having 1 to 20C atoms, or a branched or cyclic alkyl group having 3 to 20C atoms, or a branched or cyclic alkoxy group having 3 to 20C atoms, or a branched or cyclic thioalkoxy group having 3 to 20C atoms, or a silyl group, or a ketone group having 1 to 20C atoms, or an alkoxycarbonyl group having 2 to 20C atoms, or an aryloxycarbonyl group having 7 to 20C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate, a thiocyanate, an isothiocyanate, a hydroxyl group, a nitro group, a CF group₃Cl, Br, F, I, or a crosslinkable group, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems.

4. The phosphorescent host material of claim 3, wherein: ar (Ar)¹Selected from the group consisting of:

5. the phosphorescent host material of claim 1, wherein: ar (Ar)²、Ar³、Ar⁴Independently selected from the group consisting of:

wherein:

X₁at each occurrence, is independently selected from CR₉Or N;

Y₁selected from NR₉、CR₉R₁₀、SiR₉R₁₀、O、S、S＝O、S(＝O)₂；

R₉-R₁₀Independently at each occurrence, H, D, or a straight chain alkyl group having 1 to 20C atoms, or a straight chain alkyloxy group having 1 to 20C atoms, or a straight chain thioalkoxy group having 1 to 20C atoms, or a branched or cyclic alkyl group having 3 to 20C atoms, or a branched or cyclic alkoxy group having 3 to 20C atoms, or a branched or cyclic thioalkoxy group having 3 to 20C atoms, or a silyl group, or a ketone group having 1 to 20C atoms, or an alkoxycarbonyl group having 2 to 20C atoms, or an aryloxycarbonyl group having 7 to 20C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate, a thiocyanate, an isothiocyanate, a hydroxyl group, a nitro group, a CF group₃Cl, Br, F, I, or a crosslinkable group, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems.

6. The phosphorescent host material of claim 5, wherein: the general formula (1) is selected from the following structures:

7. the phosphorescent host material of claim 1, wherein: the general formula (2) is selected from any one of the following structures:

8. the phosphorescent host material of claim 7, wherein: ar (Ar)⁶、Ar⁷Selected from the group consisting of:

wherein:

X₂at each occurrence, is independently selected from CR₁₁；

Y₂Selected from NR₁₁、CR₁₁R₁₂、SiR₁₁R₁₂O or S (O) O, S, S₂；

9. The phosphorescent host material of claim 1, wherein: ar (Ar)⁵、Ar⁶、Ar⁷Wherein at least one substituent R is present, said substituent R being selected from the group consisting of:

wherein:

Ar⁸、Ar⁹、Ar¹⁰each independently represents a substituted or unsubstituted aromatic group having 6 to 30 ring atoms or a substituted or unsubstituted heteroaromatic group having 6 to 30 ring atoms;

Z⁴-Z⁷independently selected from single bond, NR₁₃、CR₁₃R₁₄、SiR₁₃R₁₄、O、C＝O、C＝NR₁₃、C＝CR₁₃、PR₁₃、P(＝O)R₁₃S, S ═ O or SO₂；

R₁₃-R₁₄Independently at each occurrence, H, D, or a straight chain alkyl group having 1 to 20C atoms, or a straight chain alkyloxy group having 1 to 20C atoms, or a straight chain thioalkoxy group having 1 to 20C atoms, or a branched or cyclic alkyl group having 3 to 20C atoms, or a branched or cyclic alkoxy group having 3 to 20C atoms, or a branched or cyclic thioalkoxy group having 3 to 20C atoms, or a silyl group, or a ketone group having 1 to 20C atoms, or an alkoxycarbonyl group having 2 to 20C atoms, or an aryloxycarbonyl group having 7 to 20C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate, a thiocyanate, an isothiocyanate, a hydroxyl group, a nitro group, a CF group₃Cl, Br, F, I, or a crosslinkable group, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems.

10. The phosphorescent host material of claim 1, wherein: the general formula (2) is selected from the following structures:

wherein: l represents a single bond, an aromatic group or an aromatic hetero group having 5 to 30 ring atoms, and the connecting position of L may be on any carbon atom on the ring.

11. The phosphorescent host material of claim 1, wherein: min (LUMO (H1) -HOMO (H2), LUMO (H2) -HOMO (H1)) is in the range of 1.9eV to 3.1 eV;

wherein: LUMO (H1) represents the lowest unoccupied orbital level of H1, HOMO (H1) represents the highest occupied orbital level of H1; LUMO (H2) represents the lowest unoccupied orbital level of H2, and HOMO (H2) represents the highest occupied orbital level of H2.

12. The phosphorescent host material of claim 1, wherein: h1 is selected from the following structures:

h2 is selected from the following structures:

13. the phosphorescent host material of claim 1, wherein: h1 and H2 form a type II semiconductor heterojunction structure.

14. A composition characterized by: comprising at least one phosphorescent host material according to any of claims 1 to 13 and at least one organic solvent.

15. An organic electronic device, characterized by: comprising a light-emitting layer, the light-emitting layer host material being selected from the phosphorescent host materials of any one of claims 1 to 13.

Technical Field

The invention relates to a functional material of an organic electronic device, in particular to a phosphorescent main body material and application thereof in the organic electronic device, in particular to a phosphorescent organic electroluminescent device.

Background

Organic Light Emitting Diodes (OLEDs), which have excellent properties such as light weight, active light emission, wide viewing angle, high contrast, high light emitting efficiency, low power consumption, easy fabrication of flexible and large-sized panels, are considered as the most promising next-generation display technology in the industry.

In order to improve the light emitting efficiency of the organic light emitting diode, various light emitting material systems based on fluorescence and phosphorescence have been developed, and the organic light emitting diode using a fluorescent material has a high reliability but is limited in its internal electroluminescence quantum efficiency to 25% under electrical excitation because the ratio of the singlet excited state to the triplet excited state of current-generated excitons is 1: 3. In contrast, the organic light emitting diode using the phosphorescent material has achieved almost 100% internal electroluminescence quantum efficiency, and thus the development of the phosphorescent material has been widely studied.

The light emitting material (guest) may be used as a light emitting material together with a host material (host) to improve color purity, light emitting efficiency, and stability. Since the host material greatly affects the efficiency and characteristics of the electroluminescent device when the host material/guest system is used as the light emitting layer of the light emitting device, the selection of the host material is important.

As for the host material, the host material mainly plays a role of energy transfer in the light-emitting layer. Host materials need to have appropriate HOMO and LUMO energy levels to be able to reduce barriers for electron and hole injection; the triplet state energy level of the host material is higher than that of the light-emitting guest material, so that energy can be prevented from rotating; the host material needs to have certain charge transfer balance capability, so that an exciton recombination region is concentrated in the center of the light-emitting layer, and high energy utilization efficiency and device stability are realized.

Currently, 4, 4' -dicarbazole-biphenyl (CBP) is known to be the most widely used host material for phosphorescent substances. In recent years, Pioneer corporation (Pioneer) and the like have developed a high-performance organic electroluminescent device using a compound such as BAlq (bis (2-methyl) -8-hydroxyquinolinato-4-phenylphenolaluminum (III)), phenanthroline (BCP), and the like as a substrate.

In the existing material design, people tend to design a dual-host material into a bipolar transmission host, which is beneficial to the balance of charge transmission, and good device performance can be obtained by using bipolar transmission molecules as the host. The performance and lifetime of the resulting devices remain to be improved.

Thus, there is still a need for improvements and developments in the art for host materials, particularly phosphorescent host solutions.

Disclosure of Invention

In view of the above-mentioned shortcomings of the prior art, the present invention aims to provide a phosphorescent host material of dual-host type and its application in organic electronic devices, aiming to solve the problems of low performance and device lifetime of the existing organic electronic devices.

The invention relates to a phosphorescent host material, which at least comprises an N-type host material H1 and a P-type host material H2, wherein the N-type host material H1 is selected from a structure shown in a general formula (1):

wherein:

Z¹selected from the group consisting of CR₁R₂、SiR₁R₂、O、C＝NR₁、C＝CR₁、PR₁、P(＝O)R₁S, S ═ O or SO₂(ii) a The P-type host material H2 is selected from a structure shown in a general formula (2):

wherein:

n is selected from 1,2,3 or 4;

Ar⁵、Ar⁶、Ar⁷each independently represents a substituted or unsubstituted aromatic group having 6 to 30 ring atoms or a substituted or unsubstituted heteroaromatic group having 6 to 30 ring atoms; z²、Z³Are independently selected from single bond and NR₄、CR₄R₅、SiR₄R₅、O、C＝O、C＝NR₄、C＝CR₄、 PR₄、P(＝O)R₄S, S ═ O or SO₂；

R₁-R₅Independently at each occurrence, H, D, or a straight chain alkyl group having 1 to 20C atoms, or a straight chain alkyloxy group having 1 to 20C atoms, or a straight chain thioalkoxy group having 1 to 20C atoms, or a branched or cyclic alkyl group having 3 to 20C atoms, or a branched or cyclic alkoxy group having 3 to 20C atoms, or a branched or cyclic thioalkoxy group having 3 to 20C atoms, or a silyl group, or a ketone group having 1 to 20C atoms, or an alkoxycarbonyl group having 2 to 20C atoms, or an aryloxycarbonyl group having 7 to 20C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate, a thiocyanate, an isothiocyanate, a hydroxyl group, a nitro group, a CF group₃Cl, Br, F, I, or a crosslinkable group, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems.

A composition comprising at least one phosphorescent host material as described above and at least one organic solvent.

An organic electronic device comprising a light-emitting layer, the light-emitting layer host material being selected from phosphorescent host materials as described above.

Has the advantages that:

the phosphorescent host material provided by the invention is used in an OLED and can provide higher luminous stability and longer service life of a device. The possible reasons for this are as follows, but not limited thereto, the N-type host material H1 of the present invention has electron transport properties; the P-type main body material has hole transmission performance, and the P-N type phosphorescent main body material has the effect of balancing charge transmission. In addition, H1 and H2 both have suitable LUMO and HOMO energy levels, while Δ E can be formed between H1 and H2 molecules_STThe small energy intermediate has high energy utilization rate, thereby improving the luminous efficiency and the service life of related devices.

Detailed Description

In order that the invention may be more fully understood, reference will now be made to the accompanying examples. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.

Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.

As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.

In the embodiments of the present invention, the Host material, the Matrix material, the Host material, and the Matrix material have the same meaning and may be interchanged.

In the embodiments of the present invention, singlet states and singlet states have the same meaning and may be interchanged.

In the present embodiment, the triplet state and the triplet state have the same meaning and are interchangeable.

In the present invention, the multiple excited states, Exciplex, and exiplex have the same meaning and are interchangeable.

In the present invention, P-type and N-type refer to the conductivity characteristics of the material, and the P-type host material functions as an electron donor (hole transport) and the N-type host material functions as an electron acceptor (electron transport). The N-type host material H1 is an electron transport type host material H1, and the P-type host material H2 is a hole transport type host material H2. In the present invention, "substituted" means that a hydrogen atom in a substituent is substituted by a substituent.

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

An aromatic group refers to a hydrocarbon group containing at least one aromatic ring. A heteroaromatic group refers to an aromatic hydrocarbon group that contains at least one heteroatom. The heteroatoms are preferably selected from Si, N, P, O, S and/or Ge, particularly preferably from Si, N, P, O and/or S. By fused ring aromatic group is meant that the rings of the aromatic group may have two or more rings in which two carbon atoms are shared by two adjacent rings, i.e., fused rings. The fused heterocyclic aromatic group means a fused ring aromatic hydrocarbon group containing at least one hetero atom. For the purposes of the present invention, aromatic or heteroaromatic radicals include not only aromatic ring systems but also non-aromatic ring systems. Thus, for example, systems such as pyridine, thiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, pyrazine, pyridazine, pyrimidine, triazine, carbene, and the like, are also considered aromatic or heterocyclic aromatic groups for the purposes of this invention. For the purposes of the present invention, fused-ring aromatic or fused-heterocyclic aromatic ring systems include not only systems of aromatic or heteroaromatic groups, but also systems in which a plurality of aromatic or heterocyclic aromatic groups may also be interrupted by short non-aromatic units (< 10% of non-H atoms, preferably less than 5% of non-H atoms, such as C, N or O atoms). Thus, for example, systems such as 9, 9' -spirobifluorene, 9, 9-diarylfluorene, triarylamines, diaryl ethers, etc., are also considered fused aromatic ring systems for the purposes of this invention.

In the embodiment of the present invention, the energy level structure of the organic material, the triplet state energy level E_THOMO, LUMO play a key role. These energy levels are described below.

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

Triplet energy level E of organic material_T1Can be measured by low temperature Time resolved luminescence spectroscopy, or can be obtained by quantum simulation calculations (e.g., by Time-dependent DFT), such as by commercial software Gaussian09W (Gaussian Inc.), specific simulation methods can be found in WO2011141110 or as described in the examples below.

Note that HOMO, LUMO, E_T1The absolute value of (c) depends on the measurement method or calculation method used, and even for the same method, different methods of evaluation, for example starting point and peak point on the CV curve, can give different HOMO/LUMO values. Thus, a reasonably meaningful comparison should be made with the same measurement method and the same evaluation method. In the description of the embodiments of the present invention, HOMO, LUMO, E_T1Is based on the simulation of the Time-dependent DFT but does not affect the application of other measurement or calculation methods.

In the present invention, (HOMO-1) is defined as the second highest occupied orbital level, (HOMO-2) is defined as the third highest occupied orbital level, and so on. (LUMO +1) is defined as the second lowest unoccupied orbital level, (LUMO +2) is the third lowest occupied orbital level, and so on.

The invention relates to a phosphorescent host material, which at least comprises an N-type (electron transport type) host material H1 and a P-type (hole transport type) host material H2, wherein the N-type host material H1 is selected from structures shown in a general formula (1):

wherein:

Z¹selected from the group consisting of CR₁R₂、SiR₁R₂、O、C＝NR₁、C＝CR₁、PR₁、P(＝O)R₁S, S ═ O or SO₂；

The P-type host material H2 is selected from a structure shown in a general formula (2):

wherein:

n is selected from 1,2,3 or 4;

Z²、Z³are independently selected from single bond and NR₄、CR₄R₅、SiR₄R₅、O、C＝O、C＝NR₄、C＝CR₄、PR₄、P(＝O)R₄S, S ═ O or SO₂；

R₁-R₅Independently at each occurrence, H, D, or a straight chain alkyl group having 1 to 20C atoms, or a straight chain alkyloxy group having 1 to 20C atoms, or a straight chain thioalkoxy group having 1 to 20C atoms, or a branched or cyclic alkyl group having 3 to 20C atoms, or a branched or cyclic alkoxy group having 3 to 20C atoms, or a branched or cyclic thioalkoxy group having 3 to 20C atoms, or a silyl group, or a ketone group having 1 to 20C atoms, or an alkoxycarbonyl group having 2 to 20C atoms, or an aryloxycarbonyl group having 7 to 20C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate, a thiocyanate, an isothiocyanate, a hydroxyl group, a nitro group, a CF group₃Cl, Br, F, I, or a crosslinkable group, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems.

In a preferred embodiment, the phosphorescent host material according to the invention comprises 3:7 to 7:3 weight percent of N-type host material H1 and P-type host material H2; more preferably, the weight percentage of the N-type host material H1 to the P-type host material H2 is 4:6-6: 4; more preferably, the weight percentage of the N-type host material H1 to the P-type host material H2 is 5: 5.

In a preferred embodiment, min (LUMO (H1) -HOMO (H2), LUMO (H2) -HOMO (H1)). ltoreq.min (E)_T(H1), E_T(H2) +0.1 eV; wherein: LUMO (H1) represents the lowest unoccupied orbital level of H1, HOMO (H1) represents the highest occupied orbital level of H1, E_T(H1) Represents the triplet energy level of H1; LUMO (H2) represents the lowest unoccupied orbital level of H2, HOMO (H2) represents the highest occupied orbital level of H2, E_T(H2) Represents the triplet energy level of H2.

More preferably, min (LUMO (H1) -HOMO (H2), LUMO (H2) -HOMO (H1)) ≦min(E_T(H1),E_T(H2))；

Further, min (LUMO (H1) -HOMO (H2), LUMO (H2) -HOMO (H1)) ≦ min (E)_T(H1),E_T(H2))-0.1eV；

Further, min (LUMO (H1) -HOMO (H2), LUMO (H2) -HOMO (H1)) ≦ min (E)_T(H1),E_T(H2))-0.2eV；

In this case, an exciplex can be formed between H1 and H2, which is more convenient for efficient charge transport in the device when used as a phosphorescent host material.

In a preferred embodiment, the above phosphorescent host material has min (LUMO (H1) -HOMO (H2), LUMO (H2) -HOMO (H1)) in the range of 1.9-3.1 eV.

In a preferred embodiment, the above phosphorescent host material has min (LUMO (H1) -HOMO (H2), LUMO (H2) -HOMO (H1)) in the range of 1.9-2.4 eV. Such host materials may be preferred as red phosphorescent host materials.

In a further preferred embodiment, the phosphorescent host material according to the invention has a min (LUMO (H1) -HOMO (H2), LUMO (H2) -HOMO (H1)) in the range from 2.4 to 2.7 eV. Such host materials may be preferred as green phosphorescent host materials.

In a further preferred embodiment, the phosphorescent host material according to the invention has a min (LUMO (H1) -HOMO (H2), LUMO (H2) -HOMO (H1)) in the range from 2.5 to 2.6 eV.

In one embodiment, the phosphorescent host material is used in an organic electronic device as a green phosphorescent host material.

In a further preferred embodiment, the phosphorescent host material according to the invention has a min (LUMO (H1) -HOMO (H2), LUMO (H2) -HOMO (H1)) in the range from 2.7 to 3.1 eV. Such host materials may be preferred as blue phosphorescent host materials.

In a certain preferred embodiment, H1 and H2 form a type II semiconductor heterojunction structure.

In a certain preferred embodiment, LUMO (H2) ≧ LUMO (H1) and HOMO (H2) ≧ HOMO (H1);

in a certain preferred embodiment, LUMO (H2) -LUMO (H1) ≧ 0.1 eV; more preferably, LUMO (H2) -LUMO (H1) ≥ 0.2 eV; more preferably, LUMO (H2) -LUMO (H1) ≧ 0.5eV.

In a certain preferred embodiment, HOMO (H2) -HOMO (H1) ≧ 0.1 eV; in a certain preferred embodiment, HOMO (H2) -HOMO (H1) ≧ 0.2 eV; in a certain preferred embodiment, HOMO (H2) -HOMO (H1) ≧ 0.3 eV; in a preferred embodiment, HOMO (H2) -HOMO (H1) ≧ 0.4 eV.

In a preferred embodiment, H1 has a smaller singlet-triplet energy level difference, better S_T(H1)-E_T(H1) Less than or equal to 0.3 eV; better S_T(H1)-E_T(H1) Less than or equal to 0.2 eV; better S_T(H1)-E_T(H1)≤0.15eV。S_T(H1) Representing the singlet energy level of H1.

In a preferred embodiment, according to the phosphorescent host material of the present invention, at least one of H1 and H2 (HOMO- (HOMO-1)) > 0.2eV, preferably 0.25eV, more preferably 0.3eV, still more preferably 0.35eV, particularly preferably 0.4eV, most preferably 0.45 eV.

In a particularly preferred embodiment, the phosphorescent host material according to the invention is characterized in that each of said H1 and H2 has a value (HOMO- (HOMO-1)). gtoreq.0.2 eV, preferably one of said H1 and H2 (HOMO- (HOMO-1)). gtoreq.0.25 eV, more preferably > 0.3eV, still more preferably > 0.35eV, very preferably > 0.4eV, most preferably > 0.45 eV.

In a further preferred embodiment, the phosphorescent host material according to the invention is characterized in that at least one of said H1 and H2 has a value ((LUMO +1) -LUMO) of ≧ 0.15eV, preferably ≧ 0.20eV, more preferably ≧ 0.25eV, still more preferably ≧ 0.30eV, very preferably ≧ 0.35eV, most preferably ≧ 0.40 eV.

In another particularly preferred embodiment, the phosphorescent host material according to the invention is characterized in that each of said H1 and H2 has ((LUMO +1) -LUMO) ≧ 0.15eV, preferably ((LUMO +1) -LUMO) ≧ 0.20eV, more preferably ≧ 0.25eV, still more preferably ≧ 0.30eV, very preferably ≧ 0.35eV, most preferably ≧ 0.40 eV.

In a certain preferred embodiment, Ar in formula (1)¹Containing at least one electron-deficient group, said electron-deficient groupThe sub-groups are selected from F, cyano or one or more of the following groups:

wherein:

n1 represents any integer of 1 to 3;

x is independently selected from CR at each occurrence₆Or N, and at least one is N;

y is selected from NR₇、CR₇R₈、SiR₇R₈、O、S、S＝O、S(＝O)₂；

M¹、M²、M³Each independently represents NR₇、CR₇R₈、SiR₇R₈、O、C＝CR₇R₈、PR₇、P(＝O)R₇、S、S＝O、S(＝O)₂Or none;

Further, the electron-deficient group is selected from one or more of F, cyano or the following groups:

in a certain preferred embodiment, Ar in formula (1)¹Selected from the group consisting of:

in one embodiment, R₆Selected from phenyl, naphthyl, biphenyl, terphenyl, deuterated phenyl or deuterated biphenyl.

In a certain preferred embodiment, Ar in formula (1)¹Selected from the group consisting of:

in a certain preferred embodiment, Ar in formula (1)²、Ar³、Ar⁴Each independently represents a substituted or unsubstituted aromatic group having 6 to 30 ring atoms or a substituted or unsubstituted heteroaromatic group having 6 to 30 ring atoms; in a certain preferred embodiment, Ar in formula (1)²、 Ar³、Ar⁴Each independently represents a substituted or unsubstituted phenyl group; in a certain preferred embodiment, Ar in formula (1)²、Ar³、Ar⁴At least one substituted or unsubstituted 10-30 condensed ring aromatic group or substituted or unsubstituted 10-30 condensed ring heteroaromatic group; in a certain preferred embodiment, Ar in formula (1)²、Ar³、Ar⁴At least one substituted or unsubstituted 10-15 condensed ring aromatic group; in a certain preferred embodiment, Ar in formula (1)²、Ar³、Ar⁴At least two groups are selected from 10-30 substituted or unsubstituted condensed ring aromatic groups or 10-30 substituted or unsubstituted condensed ring heteroaromatic groups; in thatIn a preferred embodiment, Ar in the general formula (1)²、Ar³、Ar⁴At least two aromatic groups are 10-15 fused rings which are substituted or unsubstituted.

In the present invention, said substitution means further substitution by R ', R' having the same meaning as R₁。

In a certain preferred embodiment, Ar in formula (1)²、Ar³、Ar⁴Each independently selected from the group consisting of:

wherein:

X₁at each occurrence, is independently selected from CR₉Or N;

Y₁selected from NR₉、CR₉R₁₀、SiR₉R₁₀、O、S、S＝O、S(＝O)₂；

Further, Ar in the general formula (1)²、Ar³、Ar⁴Each independently selected from the group consisting of:

in a certain preferred embodiment, Ar²、Ar³、Ar⁴Are all selected from benzene, and the general formula (1) is selected from any one of the following structures:

in a certain preferred embodiment, Ar²、Ar³、Ar⁴At least one group selected from:

in a certain preferred embodiment, Ar³、Ar⁴At least one group selected from:

in one embodiment, formula (1) is selected from any of the following structures:

in a certain preferred embodiment, Ar in formula (2)⁵Represents a substituted or unsubstituted aromatic group having 6 to 10 ring atoms or a substituted or unsubstituted heteroaromatic group having 6 to 10 ring atoms.

Further, Ar⁵Selected from the following groups:

further, the general formula (2) is selected from any one of structures (2-1) to (2-6):

in a certain preferred embodiment, n is selected from 1; preferably, n is selected from any integer from 2 to 4; more preferably, n is selected from 3 or 4.

In a certain preferred embodiment, Ar⁶、Ar⁷Selected from the group consisting of:

wherein:

X₂at each occurrence, is independently selected from CR₁₁；

Y₂Selected from NR₁₁、CR₁₁R₁₂、SiR₁₁R₁₂O or S (O) O, S, S₂；

R₉-R₁₀Independently at each occurrence, H, D, or a straight chain alkyl group having 1 to 20C atoms, or a straight chain alkyloxy group having 1 to 20C atoms, or a straight chain thioalkoxy group having 1 to 20C atoms, or a branched or cyclic alkyl group having 3 to 20C atoms, or a branched or cyclic alkoxy group having 3 to 20C atoms, or a branched or cyclic thioalkoxy group having 3 to 20C atoms, or a silyl group, or a ketone group having 1 to 20C atoms, or an alkoxycarbonyl group having 2 to 20C atoms, or an aryloxycarbonyl group having 7 to 20C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate, a thiocyanate, an isothiocyanate, a hydroxyl group, a nitro group, a CF group₃Cl, Br, F, I, orA crosslinking group, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems.

Further, Ar⁶、Ar⁷Preferably substituted or unsubstituted benzene, or substituted or unsubstituted naphthalene.

Further, Ar⁶、Ar⁷Independently selected from substituted or unsubstituted benzene, or substituted or unsubstituted naphthalene, and Ar⁶、Ar⁷At least one of them is selected from substituted or unsubstituted benzene.

In one embodiment, Ar⁶、Ar⁷Selected from benzene.

In a preferred embodiment, Z²、Z³Selected from single bonds, NR₄、CR₄R₅、SiR₄R₅O or S; when Z is²、Z³Selected from the group consisting of CR₄R₅Or SiR₄R₅When R is₄And R₅May be interconnected to form a ring.

Further, Z²、Z³At most one of which is selected from single bonds.

In a preferred embodiment, R in the general formula (2) and the general formulae (2-1) to (2-6)₃Selected from the group consisting of:

wherein: n2 is selected from any integer of 1-6; preferably, n2 is selected from any integer from 2 to 6

In a certain preferred embodiment, in the general formula (2), Ar⁵、Ar⁶、Ar⁷Wherein at least one substituent R is present, said R comprising the following groups:

wherein:

Z⁴-Z⁷independently selected from single bond, NR₁₃、CR₁₃R₁₄、SiR₁₃R₁₄、O、C＝O、C＝NR₁₃、C＝CR₁₃、PR₁₃、P(＝O)R₁₃S, S ═ O or SO₂；

Further, R comprises the following group:

further, the general formula (2) is selected from the following general formulae:

wherein: l represents a single bond, or an aromatic group with 5-30 ring atoms, or an aromatic hetero group with 5-30 ring atoms, and the connecting position of L can be any carbon atom on the ring.

Preferably, Z⁴-Z⁵One of them is selected from single bonds; preferably, Z⁶-Z⁷One of them is selected from single bonds; preferably, Z⁴-Z⁵One is selected from single bond and one is selected from NR₁₃(ii) a Preferably, Z⁶-Z⁷One is selected from single bond and one is selected from NR₁₃；

More preferably, Z⁴-Z⁵One is selected from single bond and one is selected from NR₁₃(ii) a And Z is⁶-Z⁷One is selected from single bond and one is selected from NR₁₃。

Further, the general formula (2) is selected from the following general formulae:

in another embodiment, formula (2) is selected from the following formulas:

in one embodiment, R₃、R₄Each independently selected from phenyl, naphthyl, biphenyl or terphenyl.

In a preferred embodiment, examples of phosphorescent host materials according to the present invention that may be used in H1 are as follows, and are not limited to:

in a preferred embodiment, examples of phosphorescent host materials according to the present invention that may be used in H2 are as follows, and are not limited to:

in a preferred embodiment, the phosphorescent host material has a difference in molecular weight between H1 and H2 of no more than 100Dalton, preferably no more than 80Dalton, more preferably no more than 70Dalton, more preferably no more than 60Dalton, most preferably no more than 40Dalton, and most preferably no more than 30 Dalton.

In another preferred embodiment, the phosphorescent host material, wherein the difference between sublimation temperatures of H1 and H2 is no more than 50K; more preferably the difference in sublimation temperatures does not exceed 30K; more preferably, the difference in sublimation temperature does not exceed 20K; most preferably the difference in sublimation temperatures does not exceed 10K.

In a preferred embodiment, at least one of H1 and H2 in the phosphorescent host material according to the invention has a glass transition temperature T_gNot less than 100 ℃ and in a preferred embodiment at least one of its T_gNot less than 120 ℃ and in a more preferred embodiment at least one of its T' s_g140 ℃ or more, and in a more preferred embodiment at least one of its T_g160 ℃ or more, and in a most preferred embodiment at least one of its T_g≥180℃。

In a preferred embodiment, the phosphorescent host material according to the invention is used in an evaporative OLED device. For this purpose, H1 and H2 according to the invention have molecular weights of 1000mol/kg or less, preferably 900mol/kg or less, very preferably 850mol/kg or less, more preferably 800mol/kg or less, most preferably 700mol/kg or less.

The phosphorescent Host material according to the present invention may further comprise an organic functional material, the organic functional material comprising a hole (also called hole) injection or transport material (HIM/HTM), a Hole Blocking Material (HBM), an electron injection or transport material (EIM/ETM), an Electron Blocking Material (EBM), an organic Host material (Host), a singlet emitter (fluorescent emitter), an organic thermal excitation delayed fluorescent material (TADF material), a triplet emitter (phosphorescent emitter), in particular a light emitting organometallic complex, and an organic dye. Various organic functional materials are described in detail, for example, in WO2010135519a1, US20090134784a1 and WO2011110277a1, the entire contents of this 3 patent document being hereby incorporated by reference. The organic functional material can be small molecule and high polymer material.

The invention further relates to a composition comprising at least one phosphorescent host material as described above and at least one organic solvent. The at least one organic solvent is selected from aromatic or heteroaromatic, ester, aromatic ketone or aromatic ether, aliphatic ketone or aliphatic ether, alicyclic or olefinic compound, or boric acid ester or phosphoric acid ester compound, or a mixture of two or more solvents.

In a preferred embodiment, a composition according to the invention, wherein said at least one organic solvent is selected from aromatic or heteroaromatic based solvents.

Examples of aromatic or heteroaromatic based solvents suitable for the present invention are, but not limited to: p-diisopropylbenzene, pentylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1, 4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3, 4-tetramethylbenzene, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2, 4-trichlorobenzene, 4-difluorodiphenylmethane, 1, 2-dimethoxy-4- (1-propenyl) benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α -dichlorodiphenylmethane, 4- (3-phenylpropyl) pyridine, benzyl benzoate, 1-bis (3, 4-dimethylphenyl) ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furancarboxylate, ethyl 2-furancarboxylate, and the like;

examples of aromatic ketone-based solvents suitable for the present invention are, but not limited to: 1-tetralone, 2- (phenylepoxy) tetralone, 6- (methoxy) tetralone, acetophenone, propiophenone, benzophenone, and derivatives thereof, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, and the like;

examples of aromatic ether-based solvents suitable for the present invention are, but not limited to: 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethylacetal, tetrahydro-2-phenoxy-2H-pyran, 1, 2-dimethoxy-4- (1-propenyl) benzene, 1, 4-benzodioxan, 1, 3-dipropylbenzene, 2, 5-dimethoxytoluene, 4-ethylphenetole, 1, 3-dipropoxybenzene, 1,2, 4-trimethoxybenzene, 4- (1-propenyl) -1, 2-dimethoxybenzene, 1, 3-dimethoxybenzene, glycidylphenyl ether, dibenzyl ether, 4-t-butylanisole, trans-p-propenylanisole, 1, 2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, methyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether;

in some preferred embodiments, the at least one organic solvent may be selected from: aliphatic ketones such as 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2, 5-hexanedione, 2,6, 8-trimethyl-4-nonanone, fenchylone, phorone, isophorone, di-n-amyl ketone, etc.; or aliphatic ethers such as amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, and the like.

In other preferred embodiments, the at least one organic solvent may be selected from ester-based solvents: alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkyl lactones, alkyl oleates, and the like. Octyl octanoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate are particularly preferred.

The solvents mentioned may be used alone or as a mixture of two or more organic solvents.

In certain preferred embodiments, a composition according to the present invention comprises at least one phosphorescent host material as described above and at least one organic solvent, and may further comprise another organic solvent. Examples of another organic solvent include (but are not limited to): methanol, ethanol, 2-methoxyethanol, methylene chloride, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1, 4-dioxane, acetone, methyl ethyl ketone, 1, 2-dichloroethane, 3-phenoxytoluene, 1,1, 1-trichloroethane, 1,1,2, 2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetrahydronaphthalene, decalin, indene, and/or mixtures thereof.

In some preferred embodiments, particularly suitable solvents for the present invention are those having Hansen (Hansen) solubility parameters within the following ranges:

δ_d(dispersion force) of 17.0 to 23.2MPa^1/2In particular in the range of 18.5 to 21.0MPa^1/2A range of (d);

δ_p(polar force) is 0.2 to 12.5MPa^1/2In particular in the range of 2.0 to 6.0MPa^1/2A range of (d);

δ_h(hydrogen bonding force) of 0.9 to 14.2MPa^1/2In particular in the range of 2.0 to 6.0MPa^1/2The range of (1).

The compositions according to the invention, in which the organic solvent is selected taking into account its boiling point parameter. In the invention, the boiling point of the organic solvent is more than or equal to 150 ℃; preferably equal to or more than 180 ℃; more preferably more than or equal to 200 ℃; more preferably more than or equal to 250 ℃; most preferably more than or equal to 275 ℃ or more than or equal to 300 ℃. Boiling points in these ranges are beneficial for preventing nozzle clogging in inkjet print heads. The organic solvent may be evaporated from the solvent system to form a thin film comprising the functional material.

In a preferred embodiment, the composition according to the invention is a solution.

In another preferred embodiment, the composition according to the invention is a suspension.

The invention also relates to the use of said composition as a coating or printing ink for the production of organic electronic devices, particularly preferably by a printing or coating production process.

Suitable Printing or coating techniques include, but are not limited to, ink jet Printing, letterpress, screen Printing, dip coating, spin coating, doctor blade coating, roll Printing, twist roll Printing, lithographic Printing, flexographic Printing, rotary Printing, spray coating, brush or pad Printing, slot die coating, and the like. Gravure printing, jet printing and ink jet printing are preferred. The solution or suspension may additionally include one or more components such as surface active compounds, lubricants, wetting agents, dispersants, hydrophobing agents, binders, and the like, for adjusting viscosity, film forming properties, enhancing adhesion, and the like. The printing technology and the requirements related to the solution, such as solvent and concentration, viscosity, etc.

The present invention also provides a use of the phosphorescent host material or composition as described above in an Organic electronic device, which may be selected from, but not limited to, Organic Light Emitting Diodes (OLEDs), Organic photovoltaic cells (OPVs), Organic light Emitting cells (OLEECs), Organic Field Effect Transistors (OFETs), Organic light Emitting field effect transistors (effets), Organic lasers, Organic spintronic devices, Organic sensors, and Organic Plasmon Emitting diodes (Organic plasma Emitting diodes), etc., and particularly preferably OLEDs. In the embodiment of the invention, the phosphorescent host material is preferably used for the light emitting layer of the OLED device.

The invention further relates to an organic electronic device comprising at least one phosphorescent host material or composition as described above. Furthermore, the organic electronic device comprises at least one functional layer comprising a phosphorescent host material as described above. The functional layer is selected from a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an emission layer (EML), an Electron Blocking Layer (EBL), an Electron Injection Layer (EIL), an Electron Transport Layer (ETL) and a Hole Blocking Layer (HBL); preferably, an organic electronic device comprises a light emitting layer, and the host material of the light emitting layer is selected from the phosphorescent host materials.

In a preferred embodiment, the organic electronic device according to the present invention comprises at least a cathode, an anode and a light-emitting layer between the cathode and the anode, wherein the light-emitting layer comprises a host material and a light-emitting material. In a certain preferred embodiment, the organic electronic device according to the present invention is a phosphorescent light emitting device.

In the phosphorescent light emitting device, especially the phosphorescent OLED, the phosphorescent light emitting device comprises a substrate, an anode, and at least one light emitting layer, wherein the light emitting layer material comprises a host material and a phosphorescent light emitting material, and the host material is selected from the phosphorescent host material according to the present invention, and a cathode.

The substrate may be opaque or transparent. A transparent substrate may be used to fabricate a transparent light emitting device. See, for example, Bulovic et al Nature 1996,380, p29, and Gu et al, appl.Phys.Lett.1996,68, p 2606. The substrate may be rigid or flexible. The substrate may be plastic, metal, semiconductor wafer or glass. Preferably, the substrate has a smooth surface. A substrate free of surface defects is a particularly desirable choice. In a preferred embodiment, the substrate is flexible, and may be selected from polymeric films or plastics having a glass transition temperature Tg of 150 deg.C or greater, preferably greater than 200 deg.C, more preferably greater than 250 deg.C, and most preferably greater than 300 deg.C. Examples of suitable flexible substrates are poly (ethylene terephthalate) (PET) and polyethylene glycol (2, 6-naphthalene) (PEN).

The anode may comprise a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into a Hole Injection Layer (HIL) or a Hole Transport Layer (HTL) or an emission layer. In one embodiment, the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the emitter in the light emitting layer or the p-type semiconductor material acting as a HIL or HTL or Electron Blocking Layer (EBL) is less than 0.5eV, preferably less than 0.3eV, most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to: al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), and the like. Other suitable anode materials are known and can be readily selected for use by one of ordinary skill in the art. The anode material may be deposited using any suitable technique, such as a suitable physical vapor deposition method including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like. In certain embodiments, the anode is pattern structured. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present invention.

The cathode may comprise a conductive metal or metal oxide. The cathode can easily inject electrons into the EIL or ETL or directly into the light emitting layer. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO level or conduction band level of the emitter in the light emitting layer or the n-type semiconductor material as the Electron Injection Layer (EIL) or the Electron Transport Layer (ETL) or the Hole Blocking Layer (HBL) is less than 0.5eV, preferablyIs less than 0.3eV, preferably less than 0.2 eV. In principle, all materials which can be used as cathodes in OLEDs are possible as cathode materials for the device according to the invention. Examples of cathode materials include, but are not limited to: al, Au, Ag, Ca, Ba, Mg, LiF/Al, MgAg alloy, BaF₂Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material may be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.

Phosphorescent emitter materials are also referred to as triplet emitter materials. Preferably, the phosphorescent emitter material is a metal complex having the general formula M (L ') q, wherein M is a metal atom, L', which may be the same or different at each occurrence, is an organic ligand which is bonded or coordinately linked to the metal atom M via one or more positions, and q is an integer between 1 and 6. Preferably, the triplet emitter comprises a chelating ligand, i.e. a ligand, which coordinates to the metal via at least two binding sites, particularly preferably the triplet emitter comprises two or three identical or different bidentate or polydentate ligands. Chelating ligands are advantageous for increasing the stability of the metal complex. In a preferred embodiment, the metal complexes which can be used as triplet emitters are of the form:

the metal atom M is selected from the transition metals or the lanthanides or actinides, preferably Ir, Pt, Pd, Au, Rh, Ru, Os, Re, Cu, Ag, Ni, Co, W or Eu, particularly preferably Ir, Au, Pt, W or Os.

Ar₁,Ar₂Each occurrence of the groups may be the same or different and is a cyclic group selected from a substituted or unsubstituted aromatic group having 6 to 30 ring atoms or a substituted or unsubstituted heteroaromatic group having 6 to 30 ring atoms. Wherein Ar1 contains at least one donor atom, i.e., an atom having a lone pair of electrons, such as nitrogen, through which a cyclic group is coordinately bound to the metal; wherein Ar2 contains at least one carbon atom through which a cyclic group is attached to the metal；Ar₁And Ar₂Linked together by a covalent bond, which may each carry one or more substituent groups, which may in turn be linked together by substituent groups; l', which may be the same or different at each occurrence, is a bidentate chelating ancillary ligand, preferably a monoanionic bidentate chelating ligand; q1 may be 0,1,2 or 3, preferably 2 or 3; q2 may be 0,1,2 or 3, preferably 1 or 0. Examples of organic ligands may be selected from phenylpyridine derivatives or 7, 8-benzoquinoline derivatives. All of these organic ligands may be substituted, for example, with alkyl chains or with fluorine-containing or silicon. The ancillary ligand may preferably be selected from acetone acetate or picric acid.

Examples of materials and their use for some triplet emitters can be found in WO0070655(A2), WO0141512(A1), WO0202714A2, WO0215645(A1), WO2005033244, WO2005019373, US20050258742, US20070087219, US20070252517, US2008027220, WO2009146770, US20090061681, WO2009118087, WO2010015307, WO 2014700531, WO 157157339, WO 20120120187, WO2013107487, WO2013094620, WO2013174471, WO 2014031977, WO 2014112450, WO2014007565, WO 2014024131, Baldo et al Nature (20112000), 750, Kido et al.Appl.Phys.Lett. (2124., Wright et al.J.99am.565), So et al. (1978). The entire contents of the above listed patent documents and literature are hereby incorporated by reference. Some examples of suitable triplet emitters are listed below:

the OLED may also comprise further functional layers, such as a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), a Hole Blocking Layer (HBL). Suitable materials for use in these functional layers are described in detail above and in WO2010135519a1, US20090134784a1 and WO2011110277a1, the entire contents of these 3 patent documents being hereby incorporated by reference.

The light-emitting device according to the present invention emits light at a wavelength of 300 to 1000nm, preferably 350 to 900nm, more preferably 400 to 800 nm.

The invention also relates to the use of the electroluminescent device according to the invention in various electronic devices, including, but not limited to, display devices, lighting devices, light sources, sensors, etc.

The present invention will be described in connection with preferred embodiments, but the present invention is not limited to the following embodiments, and it should be understood that the appended claims outline the scope of the present invention and those skilled in the art, guided by the inventive concept, will appreciate that certain changes may be made to the embodiments of the invention, which are intended to be covered by the spirit and scope of the appended claims.

DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION

1. Selection of organic functional materials

H1 is selected from the following structures:

(1) synthesis of Compound (1-3):