CN105176523A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDF

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CN105176523A
CN105176523A CN201510586398.6A CN201510586398A CN105176523A CN 105176523 A CN105176523 A CN 105176523A CN 201510586398 A CN201510586398 A CN 201510586398A CN 105176523 A CN105176523 A CN 105176523A
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organic electroluminescent
alkyl
aryl
organic
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CN105176523B (en
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金侈植
赵英俊
权赫柱
金奉玉
金圣珉
尹胜洙
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Rohm and Haas Electronic Materials Korea Ltd
Dow Advanced Display Materials Ltd
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Abstract

Disclosed are a novel organic electroluminescent compound and an organic electroluminescent device comprising the same. When used as host material of organic electroluminescent material of an OLED device, the disclosed organic electroluminescent compound exhibits high luminous efficiency and excellent life property of the material as compared to conventional host material. Therefore, it can be used to manufacture OLEDs having very good operation life.

Description

The organic electroluminescent device of new organic electroluminescent compounds and this compound of use
Patent application of the present invention is application number is 201310560948.8, the applying date is on March 17th, 2010, denomination of invention is the divisional application of the application for a patent for invention of " organic electroluminescent device of new organic electroluminescent compounds and this compound of use ", and foregoing invention patent application is international application no is PCT/KR2010/001647, international filing date is on March 17th, 2010, the application number entering National Phase in China is 201080022499.6, the divisional application of the application for a patent for invention that name is called " organic electroluminescent device of new organic electroluminescent compounds and this compound of use ".
Technical field
The present invention relates to novel organic electroluminescent compounds and comprise the organic electroluminescent device of this compound.More particularly, the present invention relates to the organic electroluminescent compounds of the novelty as electroluminescent material, and use them as the organic electroluminescent device of matrix (host).
Background technology
Determine that the most important factor of the luminous efficiency of OLED (organic electroluminescent LED) is the type of electroluminescent material.Although up to the present fluorescent material is widely used as electroluminescent material, from electroluminescent mechanism, exploitation phosphor material luminous efficiency is improved in theory to be up to one of best method of 4 times.
Up to the present, iridium (III) complex compound is well-known a kind of phosphor material, comprises (acac) Ir (btp) 2, Ir (ppy) 3and Firpic, respectively as red, green and blue phosphor materials.Specifically, many phosphor materials are studied in Japan, Europe and the U.S. at present.
As the substrate material of phosphorescent light-emitting materials, what be up to the present widely known by the people most is 4,4'-N, N'-bis-carbazoles-biphenyl (biphenyl) (CBP), and known applied hole blocking layer (such as BCP and BAlq) there is high efficiency OLED.Pioneer Electronic Corp. (Japan) has reported the high performance OLED of use two (2-methyl-8-quinophenol (oxine) root (quinolinato)) (p-phenyl phenol root (phenolato)) aluminium (III) (BAlq) derivative as matrix.
Although material of the prior art has advantage from luminosity, they have the thermostability of low second-order transition temperature and non-constant, so these materials often change in gas-phase deposition process under high temperature and vacuum.In OLED, definition power efficiency=(π/voltage) × current efficiency.Therefore, power efficiency and voltage are inversely proportional to, and power efficiency should be higher to obtain lower OLED watt consumption.In practice, the OLED of electrophosphorescence material is used to show its current efficiency (cd/A) obviously higher than using the OLED of fluorescence EL material.But, when the substrate material using conventional material such as BAlq and CBP as phosphor material, in power efficiency (lm/w), there is no obvious advantage, use the OLED of fluorescent material to have higher operating voltage this is because compare.And this OLED can not obtain satisfied equipment life.
Therefore, the substrate material needing exploitation stability and performance to improve further.
Summary of the invention
The description of invention technical problem
The present inventor makes great efforts the problem overcoming routine techniques, thus has invented the organic electroluminescent device that novel electroluminescent compounds realizes the equipment life with excellent luminous efficiency and obviously prolongation.
Therefore, the object of the invention is to overcome the problems referred to above and the organic electroluminescent compounds comprising skeleton is provided, obtaining higher luminous efficiency, equipment life of raising and suitable chromaticity coordinates to compare conventional substrate material.
Another object of the present invention is to provide has high-level efficiency and long-life organic electroluminescent device, and it uses this organic electroluminescent compounds as electroluminescent material.
The method of dealing with problems
Specifically, the present invention relates to the organic electroluminescent compounds represented with one of chemical formula (1)-(5) and the organic electroluminescent device comprising this compound.Compare conventional substrate material due to organic electroluminescent compounds of the present invention and better luminous efficiency and excellent life performance are provided, therefore can obtain the OLED with excellent working life.
[chemical formula 1]
[chemical formula 2]
[chemical formula 3]
[chemical formula 4]
[chemical formula 5]
Wherein,
X and Y is independently selected from N (Ar 1), O and S, wherein Ar 1can be mutually different, and when there being two or more Ar 1during group, Ar 1ar can be expressed as 1or Ar 2;
Z 1to Z 8independently selected from C (Ar 3) and N, wherein Ar 3can be mutually different, and adjacent Ar 3group can be joined together to form ring;
Ar 1and Ar 2independently selected from (Cl-C60) alkyl, (C3-C60) cycloalkyl, comprise one or more heteroatomic 5-or 6-unit Heterocyclylalkyl being selected from N, O, S, Si and P, (C7-C60) bicyclic alkyl, adamantyl, (C2-C60) thiazolinyl, (C2-C60) alkynyl, (C6-C60) aryl and (C3-C60) heteroaryl;
Ar 3independently selected from hydrogen, (Cl-C60) alkyl, halogen, cyano group, (C3-C60) cycloalkyl, comprise and be one or morely selected from N, O, S, heteroatomic 5-or the 6-unit Heterocyclylalkyl of Si and P, (C7-C60) bicyclic alkyl, adamantyl, (C2-C60) thiazolinyl, (C2-C60) alkynyl, (C6-C60) aryl, (Cl-C60) alkoxyl group, (C6-C60) aryloxy, (C3-C60) heteroaryl, (C6-C60) arylthio, (Cl-C60) alkylthio, single-or two (Cl-C30) alkylamino, single-or two (C6-C30) virtue is amino, three (Cl-C30) aIkylsilyl groups, two (Cl-C30) alkyl (C6-C30) arylsilyl groups, three (C6-C30) arylsilyl groups, single-or two (C6-C30) arylboranyl, single-or two (Cl-C60) boron alkyl alkyl, nitro and hydroxyl, and
Ar 1to Ar 3alkyl, cycloalkyl, Heterocyclylalkyl, bicyclic alkyl, adamantyl, thiazolinyl, alkynyl, aryl, alkoxyl group, aryloxy, heteroaryl, arylthio, alkylthio, alkylamino, virtue is amino, trialkylsilkl, dialkyiarylsilyl, diarye silyl, arylboranyl or boron alkyl alkyl can be replaced by the one or more substituting groups being selected from lower group further: (Cl-C60) alkyl, halogen, cyano group, (C3-C60) cycloalkyl, comprise and be one or morely selected from N, O, S, heteroatomic 5-or the 6-unit Heterocyclylalkyl of Si and P, (C7-C60) bicyclic alkyl, adamantyl, (C2-C60) thiazolinyl, (C2-C60) alkynyl, (C6-C60) aryl, (Cl-C60) alkoxyl group, (C6-C60) aryloxy, P (=O) R ar b[R aand R brepresent (Cl-C60) alkyl or (C6-C60) aryl independently] (C6-C60) aryl of replacing, (C3-C60) heteroaryl, (C6-C60) (C3-C60) heteroaryl of aryl replacement, (Cl-C60) (C3-C60) heteroaryl of alkyl replacement, (C6-C60) aryl (Cl-C60) alkyl, (C6-C60) arylthio, (Cl-C60) alkylthio, single-or two (Cl-C30) alkylamino, single-or two (C6-C30) virtue is amino, three (Cl-C30) aIkylsilyl groups, two (Cl-C30) alkyl (C6-C30) arylsilyl groups, three (C6-C30) arylsilyl groups, single-or two (C6-C30) arylboranyl, single-or two (Cl-C60) boron alkyl alkyl, nitro and hydroxyl, do not comprise such situation: X and Y is N (Ar 1) and Z 1to Z 8all C (Ar 3).
The substituting group comprising " (Cl-C60) alkyl " part as herein described can comprise 1-60 carbon atom, 1-20 carbon atom or 1-10 carbon atom.The substituting group comprising " (C6-C60) aryl " part can comprise 6-60 carbon atom, 6-20 carbon atom or 6-12 carbon atom.The substituting group comprising " (C3-C60) heteroaryl " part can comprise 3-60 carbon atom, 4-20 carbon atom or 4-12 carbon atom.The substituting group comprising " (C3-C60) cycloalkyl " part can comprise 3-60 carbon atom, 3-20 carbon atom or 3-7 carbon atom.The substituting group comprising " (C2-C60) alkenyl or alkynyl " part can comprise 2-60 carbon atom, 2-20 carbon atom or 2-10 carbon atom.
Term of the present invention " alkyl " comprises the saturated univalence hydrocarbyl of straight or branched or its combination, and they can only be made up of carbon atom and hydrogen atom.Term " alkoxyl group " represents-O-alkyl, and wherein alkyl is as defined above.
Term described herein " aryl " represent remove a hydrogen atom by aromatic hydrocarbon after the organic radical that obtains.Aryl comprises monocycle or carbocyclic fused ring system, and each ring of aryl suitably comprises 4-7, preferred 5-6 annular atoms.Also the structure of two or more aryl by chemical bonds can be comprised.Object lesson comprise phenyl, naphthyl, xenyl (biphenyl), anthryl, indenyl, fluorenyl, phenanthryl (phenanthryl), benzo [9,10] phenanthryl (triphenylenyl), pyrenyl, perylene base (perylenyl), base (chrysenyl), naphthacenyl (naphthacenyl), fluoranthene base (fluoranthenyl) etc., but be not limited thereto.
Term as herein described " heteroaryl " represents in aromatic nucleus skeletal atom that comprising 1-4 is selected from the heteroatoms of N, O and S and remaining aromatic nucleus skeletal atom is the aryl of carbon atom.The polyheteroaromatic that described heteroaryl can be 5-or 6-unit's bicyclic heteroaryl or condense with one or more phenyl ring, and can be fractional saturation.Also the structure with one or more heteroaryls connected by chemical bond can be comprised.Described heteroaryl can comprise divalent aryl, the oxidation of its heteroatoms or quaternized formation N-oxide compound, quaternary ammonium salt etc.Concrete example comprises bicyclic heteroaryl such as furyl, thienyl, pyrryl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl group, isothiazolyl, different azoles base, azoles base, di azoly, triazinyl, tetrazine base, triazolyl, tetrazyl, furazan base (furazanyl), pyridyl, pyrazinyl, pyrimidyl, pyridazinyl; Polyheteroaromatic is benzofuryl, benzothienyl, isobenzofuran-base, benzimidazolyl-, benzothiazolyl, benzisothiazole base, benzisoxa such as azoles base, benzo azoles base, pseudoindoyl, indyl, indazolyl, diazosulfide base, quinolyl, isoquinolyl, cinnolines base (cinnolinyl), quinazolyl, quinolizinyl (quinolizinyl), quinoxalinyl (quinoxalinyl), carbazyl, phenanthridinyl (phenanthridinyl), benzodioxole group (benzodioxolyl); And corresponding N-oxide compound (such as pyridyl N-oxide, quinolyl N-oxide compound); And quaternary ammonium salt, but be not limited to this.
The example of organic electroluminescent compounds of the present invention can be the compound that one of following chemical formula represents:
Wherein: Ar 1and Ar 2as in chemical formula (1)-(5) define.
In addition, the example of organic electroluminescent compounds of the present invention can be the compound that one of following chemical formula represents:
Wherein: Ar 1and Ar 2as in chemical formula (1)-(5) define.
The object lesson of organic electroluminescent compounds of the present invention can be the compound that one of following chemical formula represents:
Wherein: Ar 1and Ar 2as in chemical formula (1)-(5) define.
More particularly, Ar 1and Ar 2represent the substituting group that phenyl, 1-naphthyl or one of 2-naphthyl or following chemical formula represent independently, but they are not limited thereto.
Present invention provides a kind of organic electroluminescent device, it is by the first electrode, the second electrode and at least one deck organic layer of inserting between described first electrode and the second electrode; Wherein said organic layer comprises the organic electroluminescent compounds that one of one or more chemical formulas (1)-(5) represent.
The feature of organic electroluminescent device of the present invention is that organic layer comprises electroluminescence layer, and this electroluminescence layer comprises the compound of one of one or more chemical formulas (1)-(5) expression as electroluminescent matrix and one or more phosphorescent dopants.The not concrete restriction of described doping agent.
Organic electroluminescent device of the present invention also can comprise the compound that one or more are selected from aromatic amine compound and styryl aromatic amine compound, and the organic electroluminescent compounds that one of one or more chemical formulas (1)-(5) represent.
In organic electroluminescent device of the present invention, described organic layer also can comprise one or more and be selected from the periodic table of elements the 1st race, the 2nd race, the metal of period 4 and period 5 transition metal, lanthanide series metal and D-transition element or its complex compound, and the organic electroluminescent compounds that one of one or more chemical formulas (1)-(5) represent.Described organic layer can comprise electroluminescence layer and charge generation layer.
Except above-mentioned organic electroluminescent compounds, described organic electroluminescent device also can comprise the organic electro luminescent layer of one or more layers blue light-emitting, green glow or ruddiness, to form the organic electroluminescent device emitted white light.
The advantageous effects of invention
Organic electroluminescent compounds of the present invention demonstrates this material when being used as the substrate material of the electroluminescent organic material of OLED and has excellent luminous efficiency and good life performance, so can be manufactured the OLED with the very good berth life-span by this compound.
Embodiments of the present invention
Also further describe the present invention by referring to preparation example and embodiment, so that the luminescent properties of representational organic electroluminescent compounds of the present invention, its preparation method and electroluminescence device to be described, but be to provide these embodiments only for understanding embodiments of the present invention better, instead of be used for limiting the scope of the invention by any way.
Preparation example
Preparation example 1: prepare compound (A)
prepare compound (A-1)
Bromo-2-oil of mirbane (30g, 148.5mmol), 1-naphthalene boronic acids (1-naphtaleneboronicacid) (30.6g, 178.2mmol), Pd (PPh 3) 4(5.14g, 4.45mmol), 2MK 2cO 3the aqueous solution (297.01mmol), the mixture of toluene (500mL) and ethanol (200mL) stirs 4 hours at reflux conditions.After mixture cool to room temperature, add distilled water wherein.Gained mixture is extracted with ethyl acetate, extract dried over mgso, and underpressure distillation.Compound (A-1) (31g, 124.3mmol, 84.03%) is obtained by column purification.
Prepare compound (A-2)
The mixture return stirring of compound (A-1) (31g, 124.3mmol) and triethyl-phosphite (300mL) 10 hours.After mixture cool to room temperature, organic solvent is fallen in underpressure distillation.Add distilled water wherein, and described mixture is extracted with ethyl acetate.Extract dried over mgso, and underpressure distillation.Compound (A-2) (18g, 82.84mmol, 66.81%) is obtained by column purification.
Prepare compound (A-3)
Compound (A-2) (18g, 82.84mmol), l, 5-phenylbenzene-3-chloropyridine (26.4g, 99.41mmol), Pd (OAc) 2(1.85g, 8.28mmol), P (t-bu) 3(8.17ml, 16.5mmol, in dimethylbenzene 50%), the mixture return stirring of NaOt-bu (23.8g, 248.5mmol) and toluene (500mL) 12 hours.After described mixture cool to room temperature, add distilled water wherein, and described mixture is extracted with ethyl acetate.Extract dried over mgso, and underpressure distillation.Compound (A-3) (19g, 42.54mmol, 51.36%) is obtained by column purification.
Prepare compound (A-4)
Be dissolved in the solution of DMF (200mL) to compound (A-3) (19g, 42.54mmol) and add NBS (8.33g, 46.80mmol).After room temperature places 10 hours, organic solvent is fallen in underpressure distillation.Add distilled water wherein, and described mixture is extracted with ethyl acetate.Extract dried over mgso, and underpressure distillation.Compound (A-4) (20g, 38.06mmol, 89.47%) is obtained by column purification.
Prepare compound (A-5)
In compound (A-4) solution being dissolved in THF (200mL), n-buLi (15.22mL, 38.06mmol, in hexane 2.5M) is slowly added in-78 DEG C.Stir after 1 hour, add trimethyl borate wherein.Described mixture is slowly warmed up to room temperature, and stirs 12 hours.Add distilled water wherein, and described mixture is extracted with ethyl acetate.Extract dried over mgso, and underpressure distillation.Compound (A-5) (8g, 16.31mmol, 42.86%) is obtained by column purification.
Prepare compound (A-6)
Compound (A-5) (8g, 16.31mmol), bromo-2-oil of mirbane (3.95g, 19.57mmol), Pd (PPh 3) 4(0.56g, 0.48mmol), 2MK 2cO 3the aqueous solution (16mL, 32.62mmol), the mixture return stirring of toluene (70mL) and ethanol (20mL).Compound (A-6) (7g, 12.33mmol, 75.62%) is obtained according to the step identical with synthetic compound (A-1).
Prepare compound (A-7)
Compound (A-6) (7g, 12.33mmol) mix with triethyl-phosphite (100mL), and obtain compound (A-7) (4g, 7.46mmol, 58.33%) according to the step identical with synthetic compound (A-2).
Prepare compound (A)
Compound (A-7) (4g, 7.46mmol), iodobenzene (1.25mL, 11.20mmol), copper powder (0.71g, 11.20mmol), K 2cO 3(3.09g), 18-is preced with the mixture return stirring 15 hours of-6 (0.15g, 0.59mmol) and 1,2-dichlorobenzene (100mL).After reaction mixture cool to room temperature, organic solvent is fallen in underpressure distillation.Add distilled water wherein, and described mixture is extracted with ethyl acetate.Extract obtains compound (A) (3.6g, 5.88mmol, 78.88%) by column purification.
Preparation example 2: prepare compound (B)
Prepare compound (B-1)
Bromo-2, the 3-dinitrobenzenes (20g, 61.36mmol) of l, 4-bis-, 1-naphthalene boronic acids (26g, 153.42mmol), Pd (PPh 3) 4(3.54g, 3.06mmol), 2MK 2cO 3the aqueous solution (90mmol), the mixture of toluene (200mL) and ethanol (100mL) stirs 10 hours at reflux conditions.After described reaction mixture cool to room temperature, add distilled water wherein, and described mixture is extracted with ethyl acetate.Extract dried over mgso, and underpressure distillation.Compound (B-1) (22g, 52.32mmol, 85.28%) is obtained by column purification.
Prepare compound (B-2)
Compound (B-1) (22g, 52.32mmol) and triethyl-phosphite (200mL) mixing, and 180 DEG C of stirrings.Compound (B-2) (10g, 28.05mmol, 53.95%) is obtained according to the step identical with synthetic compound (A-2).
Prepare compound (B-3)
Compound (B-2) (10g, 28.05mmol), 2-iodine naphthalene (7.1g, 28.05mmol), copper powder (2.67g, 42.08mmol), K 2cO 3(11.63g, 84.17mmol), the mixture that 18-is preced with-6 (0.59g, 2.24mmol) and 1,2-dichlorobenzene (100mL) was in 190 DEG C of return stirrings 20 hours.After cool to room temperature, organic solvent is fallen in underpressure distillation.Add distilled water wherein, and described mixture is extracted with ethyl acetate.Extract dried over mgso, and underpressure distillation.Compound (B-3) (4g, 8.28mmol, 29.60%) is obtained by column purification.
Prepare compound (B)
To comprising the NaH (0.49g being dissolved in DMF (20mL), 12.43mmol, 60% dispersion liquid in mineral oil) solution reaction vessel in add the solution of the compound (B-3) (4g, 8.28mmol) being dissolved in DMF (20mL).After 1 hour, the solution that chloro-for 2-4,6-phenylbenzene triazines (2.66g, 9.94mmol) are dissolved in DMF (20mL) is added wherein.Stir after 12 hours, add distilled water, and obtained solid filtration under diminished pressure.Compound (B) (3.5g, 4.90mmol, 59.21%) is obtained from ethyl acetate and DMF recrystallization.
Preparation example 3: prepare compound (C)
Prepare compound (C-1)
Be dissolved in 1,2-cyclohexyl diketone (42.52g, 379.26mmol) in the solution of ethanol (1000mL) and slowly add 2-naphthyl hydrazine (20g, 126.42mmol).Add acetic acid (0.28mL, 5.05mmol) wherein, and mixture is heated to 40 DEG C.After 2 hours, cool described mixture, and add distilled water wherein.Obtained solid filtration under diminished pressure obtains compound (C-1) (17g, 67.37mmol, 53.47%).
Prepare compound (C-2)
Be dissolved in the solution of acetic acid (100mL) to compound (C-1) (17g, 67.37mmol) and add trifluoroacetic acid (10mL).After 2 hours, distilled water is added wherein in stirring at room temperature.Mixture NaOH aqueous solution neutralization, and be extracted with ethyl acetate.Extract dried over mgso, and underpressure distillation.Compound (C-2) (11g, 46.75mmol, 69.39%) is obtained by column purification.
Prepare compound (C-3)
According to the step identical with synthetic compound (B-3), obtain compound (C-3) (10g, 32.11mmol, 68.69%).
Prepare compound (C-4)
According to the step identical with synthetic compound (C-1), obtain compound (C-4) (12g, 29.88mmol, 93.07%).
Prepare compound (C-5)
According to the step identical with synthetic compound (C-2), obtain compound (C-5) (6g, 15.68mmol, 52.50%).
Prepare compound (C)
According to the step identical with synthetic compound (B), obtain compound (C) (5g, 8.14mmol, 51.95%).
Preparation example 4: prepare compound (D)
Prepare compound (D-2)
According to the step identical with synthetic example (A-1), but compound (D-1) is used to obtain compound (D-2) (11g, 38.02mmol, 89.22%).
Prepare compound (D-3)
Compound (D-3) (8g, 31.09mmol, 81.78%) is obtained according to the step identical with synthetic compound (A-2).
Prepare compound (D)
Compound (D) (6g, 12.30mmol, 38.70%) is obtained according to the step identical with synthetic compound (B).
Preparation example 5: prepare compd E and F
Prepare compound (E-2)
According to the step identical with synthetic compound (A-1), but compound (E-1) is used to obtain compound (E-2) (15g, 51.85mmol, 86.51%).
Prepare compound (E-3)
According to the step identical with synthetic compound (A-2), obtain compound (E-3) (6g, 23.31mmol, 44.97%).
Prepare compound (E)
According to the step identical with synthetic compound (B), obtain compound (E) (5g, 10.25mmol, 43.99%).
Prepare compound (F-1)
According to the step identical with synthetic compound (A-2), obtain compound (F-1) (3g, 11.65mmol, 22.48%).
Prepare compound (F)
The step identical according to synthetic compound (B), obtains compound (F) (3g, 6.15mmol, 52.81%).
Preparation example 6: prepare compound (G) and (H)
Prepare compound (G-1)
Carbazole (20g, 119.6mmol), iodobenzene (20mL, 179.41mmol), copper (11.4g, 179.41mmol), K 2cO 3(49g, 358.8mmol), the mixture that 18-is preced with-6 (2.5g, 9.56mmol) and 1,2-dichlorobenzene (100mL) stirs 12 hours in 190 DEG C.After cool to room temperature, reaction mixture underpressure distillation.Add distilled water wherein, and gained mixture is extracted with ethyl acetate.Extract dried over mgso, and underpressure distillation.Compound (G-1) (22g, 90.42mmol, 75.60%) is obtained by column purification.
Prepare compound (G-2)
According to the step identical with synthetic compound (A-4), obtain compound (G-2) (25g, 77.59mmol, 85.81%).
Prepare compound (G-3)
According to the step identical with synthetic compound (A-5), obtain compound (G-3) (11g, 38.31mmol, 49.37%).
Prepare compound (G-4)
According to the step identical with synthetic compound (A-1), obtain compound (G-4) (12g, 32.84mmol, 85.72%).
Prepare compound (G-5)
According to the step identical with synthetic compound (A-2), carry out reaction and within 4 hours, obtain compound (G-5) (6g, 17.99mmol, 54.80%).
Prepare compound (G)
According to the step identical with synthetic compound (B), obtain compound (G) (7g, 12.39mmol, 68.91%).
Prepare compound (H-1)
According to the step identical with synthetic compound (A-2), carry out reaction and within 4 hours, obtain compound (H-1) (2g, 5.99mmol, 18.26%).
Prepare compound (H)
According to the step identical with synthetic compound (B), obtain compound (H) (1.7g, 3.01mmol, 50.26%).
Organic electroluminescent compounds (TA, TB and TC) is prepared according to the step of preparation example (1)-(6).Substituting group (the Ar of these obtained organic electroluminescent compounds 1and Ar 2) and these compounds 1hNMR and MS/FAB data rows is in following table 1 and 2.
Table 1
Table 2
[embodiment 1-10] uses organic electroluminescent compounds of the present invention to manufacture OLED
Electroluminescent compounds of the present invention is used to manufacture OLED device.
First, transparency electrode ito thin film (15 Ω/) (purchased from the SCP company) that be used for OLED of being made up of glass is carried out ultrasonic cleaning with trieline, acetone, ethanol and distilled water successively, and is stored in before the use in Virahol.
Then, ITO substrate is contained in substrate folder (folder) of vacuum phase deposition equipment, to be represented by following chemical structural formula 4,4', 4 "-three (N; N-(2-naphthyl)-phenyl amino) triphenylamine (2-TNATA) is placed in the cell (cell) of vacuum phase deposition equipment, is then vented to house vacuum degree and is up to 10 -6holder.Electric current is applied to cell, 2-TNATA is evaporated, thus on ITO substrate the hole injection layer of vapour deposition 60 nano thickness.
Then, in another cell of this vacuum phase deposition equipment, add N, N'-bis-(Alpha-Naphthyl)-N, N'-phenylbenzene-4,4'-diamines (NPB), applies electric current to evaporate NPB to cell, thus on hole injection layer the hole transport layer of vapour deposition 20 nano thickness.
In a cell of vapor deposition apparatus, adding compound of the present invention, (it is 10 -6through vacuum-sublimation purifying under holder) (such as, compound TA8-H4-H2), and by electroluminescent dopant (such as, compound (piq) 2ir (acac)) add in another cell.Bi-material adulterates with the concentration of 4-10 % by mole with the evaporation of different speed, thus on hole transport layer the electroluminescence layer of vapour deposition 30 nano thickness.
Then, three (oxine) aluminium (III) (Alq) vapour deposition represented by following structural formula is the electron transport layer of 20 nano thickness, is the electron injecting layer of 1-2 nanometer thickness by oxine lithium (lithiumquinolate) (Liq) vapour deposition.Then, adopt another vacuum phase deposition equipment, the Al negative electrode of vapour deposition 150 nanometer thickness, manufacture OLED.
[embodiment 11-20] uses electroluminescent compounds of the present invention to manufacture OLED
Manufacture OLED according to the step identical with the OLED of embodiment 1-10, but use compound of the present invention (such as compound TA4-H4-H4) as the organic iridium complex (Ir (ppy) of substrate material and following chemical formulation 3) as electroluminescent dopant.
[comparative example 1 and 2] uses conventional electroluminescent material to manufacture OLED
OLED is manufactured according to the step identical with 11 with the embodiment of the present invention 1, but add two (2-methyl 8-quinophenol (oxine) root) (p-phenyl phenol root) aluminium (III) (BAlq) in another cell of vacuum phase deposition equipment, instead of electroluminescent compounds of the present invention, as substrate material.
At 1000cd/cm 2the operating voltage of the OLED that measurement embodiment 1-10 and embodiment 11-20 (they comprise organic electroluminescent compounds of the present invention) and comparative example 1 and 2 (they comprise conventional electroluminescent compound) manufacture and power efficiency, the results are shown in table 3 and 4.
From table 3 and 4, the organic electroluminescent compounds of the present invention's exploitation is compared conventional material and is had excellent performance in equipment performance.
Table 3
Table 4
As shown in Table 3, compared with conventional material, the compound of the present invention's exploitation shows excellent performance in luminosity.Compared with the equipment of the comparative example 1 with conventional material manufacture, the current capability that the equipment display that the present invention manufactures is excellent, thus operating voltage is reduced 1V or more.Compared with the equipment of comparative example 1, they also show 1.4 times that current efficiency performance is at least the former, this is because luminescent properties is improved significantly.
As shown in Table 4, when the compound of the present invention's exploitation is used as the matrix of green electroluminescent, compared with the equipment of comparative example 2, described equipment shows the much higher power efficiency of 1.6 times that are at least the former because they have excellent luminescent properties.Compared with conventional material, excellent luminescent properties is confirmed.Particularly, compared with the equipment of comparative example 1, the equipment of embodiment 14 can at the operating at voltages reducing 2.7V, and the equipment display operating voltage of embodiment 17 is 5.5V, at 1000cd/m 2power efficiency be 15.9lm/.
Therefore, electroluminescent compounds of the present invention is used to send the equipment display excellent luminance performance of ruddiness or green glow as substrate material, reduce operating voltage, cause the power efficiency of the equipment of particularly green light to increase 5.1-7.7lm/W like this, result improves watt consumption simultaneously.

Claims (7)

1. an organic electroluminescent compounds, described compound is selected from following compound:
Wherein, Ar 1and Ar 2independently selected from (C6-C60) aryl and (C3-C60) heteroaryl, Ar 1to Ar 2aryl and heteroaryl can be replaced by the one or more substituting groups being selected from lower group further: (Cl-C60) alkyl, halogen, cyano group, (C3-C60) cycloalkyl, comprise one or more heteroatomic 5-or 6-unit Heterocyclylalkyl being selected from N, O, S, Si and P, (C7-C60) bicyclic alkyl, adamantyl, (C2-C60) thiazolinyl, (C2-C60) alkynyl, (C6-C60) aryl, (Cl-C60) alkoxyl group, (C6-C60) aryloxy, P (=O) R ar b[R aand R brepresent (Cl-C60) alkyl or (C6-C60) aryl independently] (C6-C60) aryl of replacing, (C3-C60) heteroaryl, (C6-C60) (C3-C60) heteroaryl of aryl replacement, (Cl-C60) (C3-C60) heteroaryl of alkyl replacement, (C6-C60) aryl (Cl-C60) alkyl, (C6-C60) arylthio, (Cl-C60) alkylthio, single-or two (Cl-C30) alkylamino, single-or two (C6-C30) virtue is amino, three (Cl-C30) aIkylsilyl groups, two (Cl-C30) alkyl (C6-C30) arylsilyl groups, three (C6-C30) arylsilyl groups, single-or two (C6-C30) arylboranyl, single-or two (Cl-C60) boron alkyl alkyl, nitro and hydroxyl.
2. an organic electroluminescent device, described equipment comprises organic electroluminescent compounds according to claim 1.
3. organic electroluminescent device as claimed in claim 2, it is characterized in that, described equipment comprises the first electrode; Second electrode; And one or more layers organic layer inserted between described first electrode and the second electrode, described organic layer comprises one or more organic electroluminescent compounds according to claim 1 and one or more phosphorescent dopants.
4. organic electroluminescent device as claimed in claim 3, it is characterized in that, described organic layer also comprises the amine compound that one or more are selected from aromatic amine compound and styryl aromatic amine compound.
5. organic electroluminescent device as claimed in claim 3, it is characterized in that, described organic layer also comprises one or more and is selected from the periodic table of elements the 1st race, the 2nd race, the metal of period 4 and period 5 transition metal, lanthanide series metal and d-transition element or the complex compound that formed by them.
6. organic electroluminescent device as claimed in claim 3, it is characterized in that, described organic layer comprises electroluminescence layer and charge generation layer.
7. organic electroluminescent device as claimed in claim 3, it is characterized in that, described equipment is the organic electroluminescence equipment emitted white light, and described organic layer comprises the organic electro luminescent layer of one or more layers blue light-emitting, ruddiness or green glow simultaneously.
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