CN101414667A - Organic electroluminescent element and display - Google Patents
Organic electroluminescent element and display Download PDFInfo
- Publication number
- CN101414667A CN101414667A CNA2008101749695A CN200810174969A CN101414667A CN 101414667 A CN101414667 A CN 101414667A CN A2008101749695 A CNA2008101749695 A CN A2008101749695A CN 200810174969 A CN200810174969 A CN 200810174969A CN 101414667 A CN101414667 A CN 101414667A
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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Images
Abstract
The present invention relates to an organic electroluminescent element and a display device exhibiting high emission efficiency and long life. The organic electroluminescent element contains a pair of electrodes having therebetween at least one constituting layer containing a phosphorescent light emitting layer, wherein one of the constituting layer contains a compound represented by Formula (17), wherein o and p each represents an integer of 1 to 3; Ar1 and Ar2 each represents an arylene group or a divalent aromatic heterocyclic group; Z1, Z2, Z3 and Z4 each represents a 6-membered aromatic heterocyclic ring containing a nitrogen atom; and L represents a divalent linking group.
Description
The application is dividing an application of application number 200480000921.2, April 20 2004 applying date, denomination of invention " organic electroluminescent device and display unit ".
Technical field
The present invention relates to luminous efficiency height, long organic electroluminescent device and display unit of life-span.
Background technology
In the past,, electroluminescent display (ELD) is arranged as the electronic display unit of light emitting-type.As the inscape of ELD, can list inorganic el element and organic electroluminescent device (below be also referred to as organic EL).
Inorganic el element can be used as flat-type light source and uses, but for driven light-emitting element, needs ac high voltage.
On the other hand, organic EL has by negative electrode and anode the two and clips the luminescent layer that contains luminophor and constitute, it is a kind of by injecting electronics and hole and make its combination again in luminescent layer, generate exciton (exiton), the light (phosphorescence) of emitting when utilizing this exciton inactivation and luminous element, can be luminous by the voltage about number V～tens of V, and then, owing to be emissive type, visual field angular width, definition height, owing to be the complete solid-state components of film-type, gazed at from the viewpoint of save space, portability etc.
As the organic EL of developing towards practicability from now on, wish the lower and excellent in efficiency of a kind of consumption electric power of exploitation, the organic EL that high briliancy is luminous, known for example has, to stilbene derivative, micro-fluorophor mix in diphenylethyllene arylene derivatives or the triphenylethylene base arylene derivatives to reach the raising glorious degrees, prolong the technology (with reference to patent documentation 1) of component life, have by the oxine aluminum complex as host compound and to the element (with reference to patent documentation 2) of the organic luminous layer of the micro-fluorophor that wherein mixes, having by the oxine aluminum complex is element (with reference to patent documentation 3) of the organic luminous layer of pigment etc. as host compound and to the quinoline a word used for translation ketone that wherein mixes.
In the disclosed technology of above-mentioned patent documentation, in situation about using by the light that excites a heavy line to send, being used to make the generation of a heavy line exciton and triplet exciton is 25% than for the photism of 1:3 excites the generation probability of kind, the taking-up efficient of its light is about 20%, and the therefore outside limit of taking out quantum efficiency (η ext) is 5%.
But, use organic EL (with reference to non-patent literature 1) by Princeton University report by the phosphorescence that excites triplet to send since, the research of the material that demonstrates phosphorescence under the room temperature is enlivened (with reference to non-patent literature 2 and patent documentation 4).
If use and excite triplet, then the upper limit of internal quantum becomes 100%, therefore compares with the situation that excites a heavy line, to become be 4 times to luminous efficiency on principle, obtain and the roughly equal performance of cold-cathode tube, also can be applied to lighting field, therefore gazed at.For example, once doing with heavy metal complexes such as complex of iridium systems is the research (with reference to non-patent literature 3) of the synthetic chemical compound lot in center.
In addition, as dopant, once did the research (with reference to non-patent literature 2) of using three (2-phenylpyridine) iridium.
In addition, also carried out use L
2Ir (acac), for example (ppy)
2Ir (acac) is as dopant (with reference to non-patent literature 4) and use three (2-(p-methylphenyl) pyridine) iridium (Ir (ptpy)
3), three (benzo [h] quinoline) iridium (Ir (bzq)
3), Ir (bzq)
2ClP (Bu)
3Deng research (with reference to non-patent literature 5) as dopant.
In addition, in order to obtain high luminous efficiency, use the main body (ホ ス ト) (with reference to non-patent literature 6) of the compound of cavity conveying as phosphorescent compounds.
In addition, with the main body of various electron transport materials, use (with reference to non-patent literature 4 references) to the new complex of iridium that wherein mixes as phosphorescent compounds.And then, by importing hole blocking layer, obtain high luminous efficiency (with reference to non-patent literature 5).
In addition, a kind of part-structure, nitrogen-atoms or aryl that will contain nitrogenous aromatic ring compound disclosed as the center, to 3 directions or 4 chemical constitutions that direction is extended, heat stable hole transporting material (with reference to patent documentation 5).But, in the patent documentation 5, the luminous organic EL of phosphorescence is not disclosed fully.
In addition, a kind of nitrogenous aromatic ring compound and high luminescent material (with reference to patent documentation 6) of briliancy of belonging to also disclosed.But, in patent documentation 6, the luminous organic EL of phosphorescence is not disclosed fully.
Studying at present further luminous high efficiency, the life-span lengthization of using the luminous organic EL of this phosphorescence, though take out efficient but reached 20% the outside of for green emitting, approaching as theoretical limit, but only be low current zone (low briliancy zone), and in high galvanic areas (high briliancy zone), do not reach theoretical limit as yet.And then, with regard to other illuminant colour, do not obtain enough efficient as yet, therefore be necessary to improve, and, in the organic EL that develops towards the practicability direction from now on, wish further to develop low consumption electric power and excellent in efficiency, the luminous organic EL of high briliancy.Particularly, in the luminous organic EL of cyan phosphorescence, require the element of high efficiency light-emitting.
Therefore, to Yao the problem of Xie Decision be that high organic electroluminescent device of a kind of luminous efficiency and display unit are provided in this invention.And then, also provide a kind of life-span long organic electroluminescent device and display unit.
(patent documentation 1)
No. 3093796 communique of patent
(patent documentation 2)
The spy opens clear 63-264692 communique
(patent documentation 3)
Te Kaiping 3-255190 communique
(patent documentation 4)
No. 6097147 specification of United States Patent (USP)
(patent documentation 5)
Special fair 7-110940 communique
(patent documentation 6)
The spy opens the 2001-160488 communique
(non-patent literature 1)
M.A.Baldo etc., nature, 395 volumes, 151-154 page or leaf (1998)
(non-patent literature 2)
M.A.Baldo etc., nature, 403 volumes, No. 17,750-753 page or leaf (2000)
(non-patent literature 3)
S.Lamansky etc., J.Am.Chem.Soc., 123 volumes, 4304 pages (calendar year 2001)
(non-patent literature 4)
M.E.Tompson etc., The 10th International Workshopon Inorganic and Organic Electroluminescence (EL ' 00, creek pine)
(non-patent literature 5)
Moon-Jae Youn.0g, Tetsuo Tsutsui etc., The 10thInternational Workshop on Inorganic and OrganicElectroluminescence (EL ' 00, creek pine)
(non-patent literature 6)
Ikai etc., The 10th International WorkshoponInorganic and Organic Electroluminescence (EL ' 00, creek pine)
Summary of the invention
Above-mentioned purpose of the present invention reaches by following various formations.
(1) a kind of organic electroluminescent device is characterized in that, has the formation layer that comprises the phosphorescent luminescent layer at least between pair of electrodes, and the one deck at least in the above-mentioned formation layer contains the compound by following general formula (1) expression,
General formula (1)
In the formula, Z
1Expression can have substituent heteroaromatic, Z
2Expression can have substituent heteroaromatic or aromatic hydrocarbon ring, Z
3The linking group of expression divalent or simple chemical bond, R
101Expression hydrogen atom or substituting group.
(2) organic electroluminescent device described in (1) is characterized in that, by the Z in the compound of above-mentioned general formula (1) expression
1Be 6 yuan of rings.
(3) organic electroluminescent device described in (1) or (2) is characterized in that, by the Z in the compound of above-mentioned general formula (1) expression
2Be 6 yuan of rings.
(4) organic electroluminescent device described in wantonly 1 of (1)～(3) is characterized in that, by the Z in the compound of above-mentioned general formula (1) expression
3Be chemical bond.
(5) organic electroluminescent device described in wantonly 1 of (1)～(4) is characterized in that, is more than 450 by the molecular weight of the compound of above-mentioned general formula (1) expression.
(6) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (1-1) expression, general formula (1-1)
In the formula, R
501～R
507Represent hydrogen atom or substituting group independently of one another.
(7) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, the compound of above-mentioned general formula (1) expression is by following general formula (1-2) expression,
General formula (1-2)
In the formula, R
511～R
517Represent hydrogen atom or substituting group independently of one another.
(8) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (1-3) expression,
General formula (1-3)
In the formula, R
521～R
527Represent hydrogen atom or substituting group independently of one another.
(9) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (1-4) expression,
General formula (1-4)
In the formula, R
531～R
537Represent hydrogen atom or substituting group independently of one another.
(10) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (1-5) expression,
General formula (1-5)
In the formula, R
541～R
548Represent hydrogen atom or substituting group independently of one another.
(11) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (1-6) expression,
General formula (1-6)
In the formula, R
551～R
558Represent hydrogen atom or substituting group independently of one another.
(12) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (1-7) expression,
General formula (1-7)
In the formula, R
561～R
567Represent hydrogen atom or substituting group independently of one another.
(13) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (1-8) expression,
General formula (1-8)
In the formula, R
571～R
577Represent hydrogen atom or substituting group independently of one another.
(14) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (1-9) expression,
General formula (1-9)
In the formula, R represents hydrogen atom or substituting group, and in addition, a plurality of R can be identical or different separately.
(15) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (1-10) expression,
General formula (1-10)
In the formula, R represents hydrogen atom or substituting group, and in addition, a plurality of R can be identical or different separately.
(16) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, has at least one group by any expression in the following general formula (2-1)～(2-8) by the compound of above-mentioned general formula (1) expression,
General formula (2-1) general formula (2-2)
General formula (2-3) general formula (2-4)
General formula (2-5) general formula (2-6)
General formula (2-7) general formula (2-8)
In the general formula (2-1), R
502～R
507Represent hydrogen atom or substituting group independently of one another, in the general formula (2-2), R
512～R
517Represent hydrogen atom or substituting group independently of one another, in the general formula (2-3), R
522～R
527Represent hydrogen atom or substituting group independently of one another, in the general formula (2-4), R
532～R
537Represent hydrogen atom or substituting group independently of one another, in the general formula (2-5), R
542～R
548Represent hydrogen atom or substituting group independently of one another, in the general formula (2-6), R
552～R
558Represent hydrogen atom or substituting group independently of one another, in the general formula (2-7), R
562～R
567Represent hydrogen atom or substituting group independently of one another, in the general formula (2-8), R
572～R
577Represent hydrogen atom or substituting group independently of one another.
(17) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (3) expression,
General formula (3)
In the formula, R
601～R
606Represent hydrogen atom or substituting group independently of one another, but R
601～R
606In at least one expression group by above-mentioned general formula (2-1)～(2-4) expression at least one group of selecting.
(18) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (4) expression,
General formula (4)
In the formula, R
611～R
620Represent hydrogen atom or substituting group independently of one another, but R
611～R
620In at least one expression group by above-mentioned general formula (2-1)～(2-4) expression at least one group of selecting.
(19) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (5) expression,
General formula (5)
In the formula, R
621～R
623Represent hydrogen atom or substituting group independently of one another, but R
621～R
623In at least one expression group by above-mentioned general formula (2-1)～(2-4) expression at least one group of selecting.
(20) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (6) expression,
General formula (6)
In the formula, R
631～R
645Represent hydrogen atom or substituting group independently of one another, but R
631～R
645In at least one expression group by above-mentioned general formula (2-1)～(2-4) expression at least one group of selecting.
(21) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (7) expression,
General formula (7)
In the formula, R
651～R
656Represent hydrogen atom or substituting group independently of one another, but R
651～R
656In at least one expression group by above-mentioned general formula (2-1)～(2-4) expression at least one group of selecting, na represents 0～5 integer, nb represents 1～6 integer, but na and nb sum are 6.
(22) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (8) expression,
General formula (8)
In the formula, R
661～R
672Represent hydrogen atom or substituting group independently of one another, but R
661～R
672In at least one expression group by above-mentioned general formula (2-1)～(2-4) expression at least one group of selecting.
(23) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (9) expression,
General formula (9)
In the formula, R
681～R
688Represent hydrogen atom or substituting group independently of one another, but R
681～R
688In at least one expression group by above-mentioned general formula (2-1)～(2-4) expression at least one group of selecting.
(24) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (10) expression,
General formula (10)
In the formula, R
691～R
700Represent hydrogen atom or substituting group independently of one another, L
1The linking group of expression divalent, R
691～R
700In at least one expression group by above-mentioned general formula (2-1)～(2-4) expression at least one group of selecting.
(25) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (11) expression,
General formula (11)
In the formula, R
1, R
2Represent hydrogen atom or substituting group independently of one another, n, m represent 1～2 integer separately, and k, 1 represents 3～4 integer separately, still, and n+k=5 and 1+m=5.
(26) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (12) expression,
General formula (12)
In the formula, R
1, R
2Represent hydrogen atom or substituting group independently of one another, n, m represent 1～2 integer separately, and k, 1 represents 3～4 integer separately, still, and n+k=5 and 1+m=5.
(27) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (13) expression,
General formula (13)
In the formula, R
1, R
2Represent hydrogen atom or substituting group independently of one another, n, m represent 1～2 integer separately, and k, 1 represents 3～4 integer separately, still, and n+k=5 and 1+m=5.
(28) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (14) expression,
General formula (14)
In the formula, R
1, R
2Represent hydrogen atom or substituting group independently of one another, n, m represent 1～2 integer separately, and k, 1 represents 3～4 integer separately, still, and n+k=5 and 1+m=5.
(29) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (15) expression,
General formula (15)
In the formula, R
1, R
2Represent hydrogen atom or substituting group independently of one another, n, m represent 1～2 integer separately, and k, 1 represents 3～4 integer separately, still, and n+k=5 and 1+m=5, Z
1, Z
2, Z
3, Z
4Expression contains 6 yuan of heteroaromatics of at least one nitrogen-atoms separately.
(30) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (16) expression,
General formula (16)
In the formula, o, p represent 1～3 integer, Ar separately
1, Ar
2The aromatic heterocycle of representing arlydene or divalent separately, Z
1, Z
2Expression contains 6 yuan of heteroaromatics of at least one nitrogen-atoms separately, and L represents the linking group of divalent.
(31) organic electroluminescent device described in wantonly 1 of (1)～(5) is characterized in that, by the compound of above-mentioned general formula (1) expression by following general formula (17) expression,
General formula (17)
In the formula, o, p represent 1～3 integer, Ar separately
1, Ar
2Represent the arlydene of divalent or the aromatic heterocycle of divalent separately, Z
1, Z
2, Z
3, Z
4Expression contains 6 yuan of heteroaromatics of at least one nitrogen-atoms separately, and L represents the linking group of divalent.
(32) organic electroluminescent device described in wantonly 1 of (1)～(31) is characterized in that, contains the compound by above-mentioned general formula (1) expression in the above-mentioned phosphorescent luminescent layer.
(33) organic electroluminescent device described in wantonly 1 of (1)～(32) is characterized in that at least 1 layer in the above-mentioned formation layer is hole blocking layer, contains the compound by above-mentioned general formula (1) expression in the above-mentioned hole blocking layer.
(34) organic electroluminescent device described in wantonly 1 of (1)～(33) is characterized in that, sends the light of cyan (blueness).
(35) organic electroluminescent device described in wantonly 1 of (1)～(33) is characterized in that, sends the light of white.
(36) a kind of display unit is characterized in that, has (1)～organic electroluminescent device described in (35) wantonly 1.
(37) a kind of organic electroluminescent device is characterized in that, has the formation layer that comprises the phosphorescent luminescent layer at least between pair of electrodes, contains the compound by following general formula (1-11) expression in the one deck at least in the above-mentioned formation layer,
General formula (1-11)
In the formula, Z
1Expression can have substituent heteroaromatic, Z
2Expression can have substituent heteroaromatic or aromatic hydrocarbon ring, Z
3The linking group of expression divalent or simple chemical bond, L represents the linking group of divalent, can be identical or different separately by 2 groups that L connects.
(38) organic electroluminescent device described in (37) is characterized in that, by the Z in the compound of above-mentioned general formula (1-11) expression
1Be 6 yuan of rings.
(39) organic electroluminescent device described in (37) or (38) is characterized in that, by the Z in the compound of above-mentioned general formula (1-11) expression
2Be 6 yuan of rings.
(40) organic electroluminescent device described in wantonly 1 of (37)～(39) is characterized in that, by the Z in the compound of above-mentioned general formula (1-11) expression
3Be chemical bond.
(41) organic electroluminescent device described in wantonly 1 of (37)～(40) is characterized in that, is more than 450 by the molecular weight of the compound of above-mentioned general formula (1-11) expression.
(42) organic electroluminescent device described in wantonly 1 of (37)～(41) is characterized in that, contains the compound by above-mentioned general formula (1-11) expression in the above-mentioned phosphorescent luminescent layer.
(43) organic electroluminescent device described in wantonly 1 of (37)～(42) is characterized in that at least 1 layer in the above-mentioned formation layer is hole blocking layer, contains the compound by above-mentioned general formula (1-11) expression in the above-mentioned hole blocking layer.
(44) organic electroluminescent device described in wantonly 1 of (37)～(43) is characterized in that, sends the light of cyan.
(45) organic electroluminescent device described in wantonly 1 of (37)～(43) is characterized in that, sends the light of white.
(46) a kind of display unit is characterized in that, possesses (37)～organic electroluminescent device described in (45) wantonly 1.
(47) a kind of organic electroluminescent device is characterized in that, has the formation layer that comprises the phosphorescent luminescent layer at least between pair of electrodes, and the one deck at least in the above-mentioned formation layer contains the compound by following general formula (1-12) expression,
General formula (1-12)
In the formula, R
102Expression can have substituent alkyl, can have substituent cycloalkyl, can have substituent aryl or can have substituent heterocyclic radical, Z
4, Z
5Expression independently of one another is used to form 5～7 yuan the necessary atom group of nitrogen heterocyclic ring structure, Z
3The linking group of expression divalent or simple chemical bond.
(48) organic electroluminescent device described in (47) is characterized in that, by the Z in the compound of above-mentioned general formula (1-12) expression
3Be chemical bond.
(49) organic electroluminescent device described in (47) or (48) is characterized in that, is more than 450 by the molecular weight of the compound of above-mentioned general formula (1-12) expression.
(50) organic electroluminescent device described in wantonly 1 of (47)～(49) is characterized in that, above-mentioned phosphorescent luminescent layer contains the compound by above-mentioned general formula (1-12) expression.
(51) organic electroluminescent device described in wantonly 1 of (47)～(50) is characterized in that at least 1 layer in the above-mentioned formation layer is hole blocking layer, and above-mentioned hole blocking layer contains the compound by above-mentioned general formula (1-12) expression.
(52) organic electroluminescent device described in wantonly 1 of (47)～(51) is characterized in that, sends the light of cyan.
(53) organic electroluminescent device described in wantonly 1 of (47)～(51) is characterized in that, sends the light of white.
(54) a kind of display unit is characterized in that, possesses (47)～organic electroluminescent device described in (53) wantonly 1.
(55) a kind of organic electroluminescent device is characterized in that, has the formation layer that comprises the phosphorescent luminescent layer at least between pair of electrodes, and the one deck at least in the above-mentioned formation layer contains the compound by following general formula (1-13) expression,
General formula (1-13)
In the formula, R
103Expression can have substituent alkyl, can have substituent cycloalkyl, can have substituent aryl or can have substituent heterocyclic radical, R
104Expression hydrogen atom or substituting group, Z
6, Z
7Expression is used to form 5～7 yuan the necessary atom group of ring structure separately.
(56) organic electroluminescent device described in (55) is characterized in that, by the Z in the compound of above-mentioned general formula (1-13) expression
6Be 6 yuan of rings.
(57) organic electroluminescent device described in (55) or (56) is characterized in that, by the Z in the compound of above-mentioned general formula (1-13) expression
7Be 6 yuan of rings.
(58) organic electroluminescent device described in wantonly 1 of (55)～(57) is characterized in that, is more than 450 by the molecular weight of the compound of above-mentioned general formula (1-13) expression.
(59) organic electroluminescent device described in wantonly 1 of (55)～(58) is characterized in that, above-mentioned phosphorescent luminescent layer contains the compound by above-mentioned general formula (1-13) expression.
(60) organic electroluminescent device described in wantonly 1 of (55)～(59) is characterized in that at least 1 layer in the above-mentioned formation layer is hole blocking layer, and above-mentioned hole blocking layer contains the compound by above-mentioned general formula (1-13) expression.
(61) organic electroluminescent device described in wantonly 1 of (55)～(60) is characterized in that, sends the light of cyan.
(62) organic electroluminescent device described in wantonly 1 of (55)～(60) is characterized in that, sends the light of white.
(63) a kind of display unit is characterized in that, possesses (55)～organic electroluminescent device described in (62) wantonly 1.
Description of drawings
Fig. 1 is the ideograph that the display unit that an example is made of organic EL is shown.
Fig. 2 is the ideograph of display part.
Fig. 3 is the ideograph of pixel.
Fig. 4 is the ideograph of the full color display of passive (パ Star シ Block) matrix-style.
Embodiment
Each related in the present invention inscape below at length is described successively.
" organic EL material "
Each related compound among the present invention below is described.
" by the compound of general formula (1) expression "
The related in the present invention compound by general formula (1) expression below is described.
Processes such as the inventor study intensively, and found that, use the organic EL by the compound of above-mentioned general formula (1) expression, and its luminous efficiency improves.And then, use organic EL by the compound of above-mentioned general formula (1) expression, its life-span prolongs.
In the above-mentioned general formula (1), Z
1Expression can have substituent heteroaromatic, Z
2Expression can have substituent heteroaromatic or aromatic hydrocarbon ring, Z
3The linking group of expression divalent or simple chemical bond.R
101Expression hydrogen atom or substituting group.
In the above-mentioned general formula (1), as Z
1, Z
2The heteroaromatic of expression can list ring that the carbon atom of the hydrocarbon ring that constitutes furan nucleus, thiphene ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, benzimidazole Huan, oxadiazole ring, triazole ring, imidazole ring, pyrazoles ring, thiazole ring, indole ring, benzimidazole ring, benzothiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, phthalazines ring, carbazole ring, carboline ring, carboline ring further replaces by nitrogen-atoms etc.And then above-mentioned heteroaromatic can have following R
101The substituting group of expression.
In the above-mentioned general formula (1), as Z
2The aromatic hydrocarbon ring of expression, can list phenyl ring, cyclohexyl biphenyl, naphthalene nucleus, Azulene (ア ズ レ Application azulene) ring, anthracene nucleus, phenanthrene (Off エ Na Application ト レ Application phenanthrene) ring, pyrene ring,
(Network リ セ Application chrysene) ring, aphthacene (Na Off セ Application naphthacene) ring, three adjacent inferior phenyl ring, the ortho-terphenyl ring, the meta-terphenyl ring, the para-terpheny ring, acenaphthene ring guan (コ ロ ネ Application coronene) ring, the fluorenes ring, fluoranthene (Off Le オ ラ Application ト レ Application fluoranthrene?) ring, the aphthacene ring, pentacene (ペ Application セ Application pentacene) ring perylene ring, pentaphene (ペ Application Off エ Application pentphene) ring Pi (ピ セ Application picene) ring, the pyrene ring, the pyrrole anthracene nucleus, ア Application ス ラ ア Application ト レ Application ring etc.And then above-mentioned aromatic hydrocarbon ring can have following R
101The substituting group of expression.
In the general formula (1), as R
101The substituting group of expression, (for example can list alkyl, methyl, ethyl, propyl group, isopropyl, the tert-butyl group, amyl group, hexyl, octyl group, dodecyl, tridecyl, myristyl, pentadecyl etc.), cycloalkyl (for example, cyclopenta, cyclohexyl etc.), alkenyl (for example, vinyl, pi-allyl etc.), alkynyl (for example, acetenyl, propargyl etc.); Aryl (for example; phenyl; naphthyl etc.); aromatic heterocycle (for example; furyl; thienyl; pyridine radicals; pyridazinyl; pyrimidine radicals; pyrazinyl; triazine radical; imidazole radicals; pyrazolyl; thiazolyl; quinazolyl; phthalazinyl etc.); heterocyclic radical (for example; pyrrolidinyl; imidazolidinyl; morpholinyl; oxazole alkyl etc.); alkoxyl (for example; methoxyl group; ethyoxyl; propoxyl group; amoxy; own oxygen base; octyloxy; dodecyloxy etc.); cycloalkyloxy (for example; cyclopentyloxy; cyclohexyloxy etc.); aryloxy group (for example; phenoxy group; naphthoxy etc.); alkylthio group (for example; methyl mercapto; ethylmercapto group; the rosickyite base; penta sulfenyl; own sulfenyl; hot sulfenyl; dodecane sulfenyl etc.); cycloalkylthio (for example; encircle penta sulfenyl; hexamethylene sulfenyl etc.); arylthio (for example; thiophenyl; naphthalene sulfenyl etc.); alkoxy carbonyl (for example; methoxycarbonyl; ethoxy carbonyl; butoxy carbonyl; carbonyl octyloxy; dodecyloxy carbonyl etc.); aryloxycarbonyl (for example; phenyloxycarbonyl; naphthoxy carbonyl etc.); sulfamoyl (for example; amino-sulfonyl; the methylamino sulfonyl; the dimethylamino sulfonyl; the fourth amino-sulfonyl; own amino-sulfonyl; the hexamethylene amino-sulfonyl; hot amino-sulfonyl; the dodecane amino-sulfonyl; the phenylsulfamoyl base; the naphthylamino sulfonyl; 2-pyridinylamino sulfonyl etc.); acyl group (for example; acetyl group; the ethyl carbonyl; the propyl group carbonyl; the amyl group carbonyl; cyclohexyl-carbonyl; the octyl group carbonyl; 2-ethylhexyl carbonyl; the dodecyl carbonyl; phenylcarbonyl group; naphthyl carbonyl; pyridine radicals carbonyl etc.); acyloxy (for example; acetoxyl group; ethyl oxy carbonyl; butyl carbonyl oxygen base; octyl group carbonyl oxygen base; dodecyl carbonyl oxygen base; phenyl carbonyl oxygen base etc.); acylamino-(for example; the methyl carbonyl amino; the ethyl carbonyl amino; the dimethyl carbonyl amino; carbonyl propyl amino; the amyl group carbonyl amino; the cyclohexyl carbonyl amino; 2-ethylhexyl carbonyl amino; the octyl group carbonyl amino; the dodecyl carbonyl amino; the phenyl carbonyl amino; naphthyl carbonyl amino etc.); carbamoyl (for example; amino carbonyl; amino-carbonyl; the dimethylamino carbonyl; third amino carbonyl; penta amino carbonyl; carbonyl amino-cyclohexanone; hot amino carbonyl; the own amino carbonyl of 2-ethyl; the dodecane amino carbonyl; the phenylamino carbonyl; the naphthylamino carbonyl; 2-pyridinylamino carbonyl etc.); urea groups (for example; the methyl urea groups; the ethyl urea groups; the amyl group urea groups; the cyclohexyl urea groups; the octyl group urea groups; the dodecyl urea groups; the phenyl urea groups; the naphthyl urea groups; 2-pyridinylamino urea groups etc.); sulfinyl (for example; methyl sulfinyl; the ethylsulfinyl-1 base; the butyl sulfinyl; the cyclohexyl sulfinyl; 2-ethylhexyl sulfinyl; the dodecyl sulfinyl; the phenyl sulfinyl; the naphthyl sulfinyl; 2-pyridylsulfinyl etc.); alkyl sulphonyl (for example; methyl sulphonyl; ethylsulfonyl; the butyl sulfonyl; the cyclohexyl sulfonyl; 2-ethylhexyl sulfonyl; dodecyl sulfonyl etc.); aryl sulfonyl (phenyl sulfonyl; the naphthyl sulfonyl; 2-pyridyl sulfonyl etc.); amino (for example; amino; ethylamino; dimethylamino; fourth amino; encircle penta amino; oneself is amino for the 2-ethyl; dodecane amino; anilino-; naphthylamino; 2-pyridinylamino etc.); halogen atom (for example; fluorine atom; the chlorine atom; bromine atoms etc.); the fluoro alkyl (for example; the fluoro methyl; trifluoromethyl; pentafluoroethyl group; pentafluorophenyl group etc.); cyano group; nitro; hydroxyl; sulfydryl; silicyl (for example, trimethyl silyl; the triisopropyl silicyl; the triphenyl silicyl; diethylamino phenyl base silicyl etc.) etc.
These substituting groups also can further be replaced by above-mentioned substituting group.In addition, these substituting groups also can form ring by a plurality of mutual bondings.
As preferred substituted, be alkyl, cycloalkyl, fluoro alkyl, aryl, aromatic heterocycle.
Linking group as divalent, except the alkyl of alkylidene, alkenylene, alkynylene, arlydene etc., can also contain hetero-atom, and, can be from resembling thiophene-2,5-two bases, pyrazine-2, the divalent linking group of the compound with heteroaromatic (being also referred to as heteroaromatic compound) of 3-two Kina samples also can be chalcogen (the カ Le コ ゲ Application chalcogen) atom of oxygen or sulphur etc.In addition, also can be to resemble the group that alkyl imino, dialkyl silane two bases and diaryl germane (ゲ Le マ Application germane) two Kina samples cooperate hetero-atom to be formed by connecting.
So-called singly-bound is the chemical bond of the substituting group Direct Bonding that will will connect.
Among the present invention, the Z of above-mentioned general formula (1)
1Be preferably 6 yuan of rings.Thus, can further improve luminous efficiency.And then the life of can further lengthening the life is long.
In addition, among the present invention, the Z of above-mentioned general formula (1)
2Be preferably 6 yuan of rings.Thus, can further improve luminous efficiency.And then the life of can further lengthening the life is long.
And then, by making the Z of above-mentioned general formula (1)
1And Z
2Being all 6 yuan of rings, can further improving the luminous efficiency aspect, is preferred therefore.And then, because the life of can further lengthening the life is long, also be preferred therefore.
In the compound by above-mentioned general formula (1) expression, preferably respectively by the compound of above-mentioned general formula (1-1)～(1-13) expression.
In the above-mentioned general formula (1-1), R
501～R
507Represent hydrogen atom or substituting group independently of one another.
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (1-1) expression.And then, can make longer organic EL of life-span.
In the above-mentioned general formula (1-2), R
511～R
517Represent hydrogen atom or substituting group independently of one another.
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (1-2) expression.And then, can make longer organic EL of life-span.
In the above-mentioned general formula (1-3), R
521～R
527Represent hydrogen atom or substituting group independently of one another.
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (1-3) expression.And then, can make longer organic EL of life-span.
In the above-mentioned general formula (1-4), R
531～R
537Represent hydrogen atom or substituting group independently of one another.
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (1-4) expression.And then, can make longer organic EL of life-span.
In the above-mentioned general formula (1-5), R
541～R
548Represent hydrogen atom or substituting group independently of one another.
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (1-5) expression.And then, can make longer organic EL of life-span.
In the above-mentioned general formula (1-6), R
551～R
558Represent hydrogen atom or substituting group independently of one another.
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (1-6) expression.And then, can make longer organic EL of life-span.
In the above-mentioned general formula (1-7), R
561～R
567Represent hydrogen atom or substituting group independently of one another.
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (1-7) expression.And then, can make longer organic EL of life-span.
In the above-mentioned general formula (1-8), R
571～R
577Represent hydrogen atom or substituting group independently of one another.
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (1-8) expression.And then, can make longer organic EL of life-span.
In the above-mentioned general formula (1-9), R represents hydrogen atom or substituting group.In addition, a plurality of R can be identical or different separately.
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (1-9) expression.And then, can make longer organic EL of life-span.
In the above-mentioned general formula (1-10), R represents hydrogen atom or substituting group.In addition, a plurality of R can be identical or different separately.
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (1-10) expression.And then, can make longer organic EL of life-span.
In the above-mentioned general formula (1-11), Z
1Expression can have substituent heteroaromatic, Z
2Expression can have substituent heteroaromatic or aromatic hydrocarbon ring, Z
3The linking group of expression divalent or simple chemical bond.L represents the linking group of divalent.Can be identical or different separately with 2 groups that L connects.
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (1-11) expression.And then, can make longer organic EL of life-span.
In the above-mentioned general formula (1-12), R
102Expression can have substituent alkyl, can have substituent cycloalkyl, can have substituent aryl or can have substituent heterocyclic radical.Z
4, Z
5Expression independently of one another is used to form 5～7 yuan the necessary atom group of nitrogen heterocyclic ring structure.Z
3The linking group of expression divalent or simple chemical bond.
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (1-12) expression.And then, can make longer organic EL of life-span.
In the above-mentioned general formula (1-13), R
103Expression can have substituent alkyl, can have substituent cycloalkyl, can have substituent aryl or can have substituent heterocyclic radical.R
104Expression hydrogen atom or substituting group.Z
6, Z
7Expression is used to form 5～7 yuan the necessary atom group of ring structure respectively.
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (1-13) expression.And then, can make longer organic EL of life-span.
Herein, the substituting group that the compound of being represented respectively by above-mentioned general formula (1-1)～(1-13) can also have in addition is with the R in the compound of being represented by above-mentioned general formula (1)
101The substituent implication of expression is identical.
In addition, in the compound by above-mentioned general formula (1) expression, preferably has the compound of at least one group of representing by the arbitrary general formula of above-mentioned general formula (2-1)～(2-8).Especially, more preferably in molecule, have 2～4 represented groups of arbitrary general formula by above-mentioned general formula (2-1)～(2-8).At this moment, be included in the structure by above-mentioned general formula (1) expression, remove R
101Remainder in addition is replaced by the situation of above-mentioned general formula (2-1)～(2-8).
At this moment, consider from the aspect that obtains effect of the present invention, especially preferably the compound of representing by above-mentioned general formula (3)～(17).
In the above-mentioned general formula (3), R
601～R
606Expression hydrogen atom or substituting group, but R
601～R
606In at least one expression by any represented group of above-mentioned general formula (2-1)～(2-4).
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (3) expression.And then, can make longer organic EL of life-span.
In the above-mentioned general formula (4), R
611～R
620Expression hydrogen atom or substituting group, but R
611～R
620In at least one expression by any represented group of above-mentioned general formula (2-1)～(2-4).
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (4) expression.And then, can make longer organic EL of life-span.
In the above-mentioned general formula (5), R
621～R
623Expression hydrogen atom or substituting group, but R
611～R
620In at least one expression by any represented group of above-mentioned general formula (2-1)～(2-4).
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (5) expression.And then, can make longer organic EL of life-span.
In the above-mentioned general formula (6), R
631～R
645Expression hydrogen atom or substituting group, but R
631～R
645In at least one expression by any represented group of above-mentioned general formula (2-1)～(2-4).
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (6) expression.And then, can make longer organic EL of life-span.
In the above-mentioned general formula (7), R
651～R
656Expression hydrogen atom or substituting group, but R
651～R
656In at least one expression by any represented group of above-mentioned general formula (2-1)～(2-4).Na represents 0～5 integer, and nb represents 1～6 integer, but na and nb sum are 6.
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (7) expression.And then, can make longer organic EL of life-span.
In the above-mentioned general formula (8), R
661～R
672Expression hydrogen atom or substituting group, but R
661～R
672In at least one expression by any represented group of above-mentioned general formula (2-1)～(2-4).
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (8) expression.And then, can make longer organic EL of life-span.
In the above-mentioned general formula (9), R
681～R
688Expression hydrogen atom or substituting group, but R
681～R
688In at least one expression by any represented group of above-mentioned general formula (2-1)～(2-4).
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (9) expression.And then, can make longer organic EL of life-span.
In the above-mentioned general formula (10), R
691～R
700Expression hydrogen atom or substituting group, but R
691～R
700In at least one expression by any represented group of above-mentioned general formula (2-1)～(2-4).
In the above-mentioned general formula (10), as L
1The divalent linking group of expression, (for example can list alkylidene, ethylidene, trimethylene, tetramethylene, propylidene, the ethyl ethylidene, pentamethylene, hexa-methylene, 2,2, the 4-tri-methyl hexamethylene, heptamethylene, eight methylene, nine methylene, decamethylene, 11 methylene, ten dimethylenes, cyclohexylidene (for example, 1,6-cyclohexane two bases etc.), cyclopentylene (for example, 1,5-pentamethylene two bases etc.) etc.), alkenylene (for example, ethenylidene, allylidene etc.), alkynylene (for example, ethynylene, the inferior pentynyl of 3-etc.), the alkyl of arlydene etc., in addition, also can list contain heteroatomic group (for example ,-O-, the divalent group that contains chalcogen of-S-etc.,-N (R)-Ji, herein, R represents hydrogen atom or alkyl, R in this alkyl and the above-mentioned general formula (1)
101The implication of the alkyl of expression is identical) etc.
In addition, in each group of above-mentioned alkylidene, alkenylene, alkynylene, arlydene, at least one in the carbon atom of formation divalent linking group also can be by chalcogen (oxygen, sulphur etc.) or above-mentioned-N (R)-replacements such as Ji.
And then, as L
1The divalent linking group of expression, can use the group that for example has the divalent heterocyclic radical, can list for example oxazole two bases, pyrimidine two bases, pyridazine two bases, pyrans two bases, pyrrolin two bases, imidazoline two bases, imidazolidine two bases, pyrazolidine two bases, pyrazoline two bases, piperidines two bases, piperazine two bases, morpholine two bases, quinuclidine two bases etc., in addition, also can be from resembling thiophene-2,5-two bases, pyrazine-2, the divalent linking group of the compound with heteroaromatic (being also referred to as heteroaromatic compound) of 3-two Kina samples.
In addition, also can be to contain to resemble that alkyl imino, dialkyl silane two bases, diaryl germane two Kina samples cooperate hetero-atom and the group that connects.
By using compound, can make the higher organic EL of luminous efficiency by above-mentioned general formula (10) expression.And then, can make longer organic EL of life-span.
Respectively by in the compound that above-mentioned general formula (11)～general formula (15) is represented separately, as R
1, R
2Biao Shi substituting group respectively is with R in the above-mentioned general formula (1)
101The substituent implication of expression is identical.
In the above-mentioned general formula (15), as Z
1, Z
2, Z
3, Z
4Respectively expression, contain 6 yuan of heteroaromatics of at least one nitrogen-atoms separately, can list for example pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring etc.
In the above-mentioned general formula (16), as Z
1, Z
2Respectively expression, contain 6 yuan of heteroaromatics of at least one nitrogen-atoms separately, can list for example pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring etc.
In the above-mentioned general formula (16), as Ar
1, Ar
2Biao Shi arlydene respectively, can list adjacent phenylene, metaphenylene, (for example to phenylene, naphthalene two bases, anthracene two bases, aphthacene two bases, pyrene two bases, naphthyl naphthalene two bases, biphenyl two bases, 3,3 '-biphenyl two bases, 3,6-biphenyl two bases etc.), terphenyl two bases, connection tetraphenyl two bases, キ Application Network Off エ ニ Le two bases, セ キ シ Off エ ニ Le two bases, connection seven phenyl two bases, connection octaphenyl two bases, connection nine phenyl two bases, connection ten phenyl two bases etc.In addition, above-mentioned arlydene can further have following substituting group.
In the above-mentioned general formula (16), Ar
1, Ar
2Biao Shi divalent aromatic heterocycle respectively, the divalent group that the ring that can list furan nucleus, thiphene ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, benzimidazole Huan, oxadiazole ring, triazole ring, imidazole ring, pyrazoles ring, thiazole ring, indole ring, benzimidazole ring, benzothiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, phthalazines ring, carbazole ring, carboline ring, is further replaced by the carbon atom of the hydrocarbon ring that constitutes the carboline ring by nitrogen-atoms etc. is derived.And then above-mentioned aromatic heterocycle can have by above-mentioned R
101The substituting group of expression.
In the above-mentioned general formula (16), as the divalent linking group of representing by L, with L in the above-mentioned general formula (10)
1The implication of divalent linking group of expression is identical, but be preferably alkylidene ,-O-,-the divalent group that contains chalcogen of S-etc., most preferably be alkylidene.
In the above-mentioned general formula (17), by Ar
1, Ar
2Biao Shi arlydene respectively is with Ar in the above-mentioned general formula (16)
1, Ar
2The implication of Biao Shi arlydene is identical respectively.
In the above-mentioned general formula (17), by Ar
1, Ar
2Biao Shi aromatic heterocycle respectively is with Ar in the above-mentioned general formula (16)
1, Ar
2The implication of Biao Shi divalent aromatic heterocycle is identical respectively.
In the above-mentioned general formula (17), as by Z
1, Z
2, Z
3, Z
4Respectively expression, contain 6 yuan of heteroaromatics of at least one nitrogen-atoms separately, for example can list pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring etc.
In the above-mentioned general formula (17), as the divalent linking group of representing by L, with L in the above-mentioned general formula (10)
1The implication of divalent linking group of expression is identical, be preferably alkylidene ,-O-,-the divalent group that contains chalcogen of S-etc., most preferably be alkylidene.
Illustrate below compound related among the present invention or, the concrete example of related compound among the present invention, but the present invention is not subjected to their qualification.
Compound center framework A
Compound center framework A
Compound center framework A
The representative synthesis example of compound related among compound related among the present invention or the present invention is shown below, but the present invention is not subjected to their qualification.
" synthesizing of exemplary compounds 73 "
With 4,4 '-diiodobiphenyl 6.87g, B-carboline 6.00g add N to, among the N-dimethylacetylamide 50ml, add copper powder 4.5g, potash 7.36g, reflux 15 hours in this mixed liquor.Put and add entry and chloroform, the elimination insoluble matter after cold.Organic layer is separated, and after water, the saturated common salt water washing, decompression concentrates down, and the residue that obtains is dissolved in the acetate, after the charcoal treatment, carries out recrystallization, obtains the colourless crystallization 4.2g of exemplary compounds 73.
The structure of exemplary compounds 73 is used
1H-NMR spectrum and mass spectrum are confirmed.The physical data of exemplary compounds 73, the spectrum data as follows.
200 ℃ of colourless crystallization, fusing points
MS(FAB)m/z：487(M
+1)
1H-NMR(400MHz，CDCl
3)：δ/ppm?7.3-7.5(m、2H)、7.5-7.6(m，4H)、7.7-7.8(m，4H)、7.9-8.0(m，4H)、8.06(d，J＝5.1Hz，2H)、8.24(d，J＝7.8Hz，2H)、8.56(d，J＝5.1Hz，2H)、8.96(s，2H)
" synthesizing of exemplary compounds 74 "
Acid chloride 0.32g, tri-butyl phosphine 1.17g are dissolved among the dry toluene 10ml, add sodium borohydride 50mg, after at room temperature stirring 10 minutes, add δ-carboline 5.00g, 4,4 '-diiodobiphenyl 5.87g, sodium tert-butoxide 3.42g, be scattered among the anhydrous dimethyl benzene 50ml, under blanket of nitrogen, under reflux temperature, stirred 10 hours.With the reactant mixture that obtains put cold after, add chloroform and water, organic layer is separated, after organic layer water, the saturated common salt water washing, decompression concentrates down, the residue that obtains is dissolved in the oxolane, after the execution charcoal treatment, carry out recrystallization, obtain the colourless crystallization 5.0g of exemplary compounds 74.
The structure of exemplary compounds 74 is used
1H-NMR spectrum and mass spectrum are confirmed.The physical data of exemplary compounds 74, the spectrum data as follows.
MS(FAB)m/z：487(M
+1)
1H-NMR(400MHz，CDCl
3)：δ/ppm?7.37(dd，J＝4.7Hz，J＝8.3Hz，2H)、7.4-7.5(m，2H)、7.5-7.6(m，4H)、7.7-7.8(m，4H)、7.81(dd，J＝1.2Hz，J＝8.3Hz，2H)、7.9-8.0(m，4H)、8.48(d，J＝7.8Hz，2H)，8.65(dd，J＝1.2Hz，J＝4.6Hz，2H)
" synthesizing of exemplary compounds 60 "
With 4,4 '-diiodobiphenyl 6.87g, gamma-carbolines 6.00g add N to, among the N-dimethylacetylamide 50ml, add copper powder 4.5g, potash 7.36g, reflux 15 hours in this mixed liquor.Put and add entry and chloroform, the elimination insoluble matter after cold.Organic layer is separated, and after water, the saturated common salt water washing, decompression concentrates down, after the residue that obtains is adsorbed with silica gel chromatograph, makes its crystallization in carrene/cyclohexane, obtains the colourless crystallization 4.3g of exemplary compounds 60.
The structure of exemplary compounds 60 is used
1H-NMR spectrum and mass spectrum are confirmed.The physical data of exemplary compounds 60, the spectrum data as follows.
MS(FAB)m/z：487(M
+1)
1H-NMR(400MHz，CDCl
3)：δ/ppm?7.4-7.4(m，4H)、7.4-7.5(m，4H)、7.7-7.8(m，4H)7.9-8.0(m，4H)、8.25(d，J＝7.8Hz，2H)、8.57(d，J＝5.6Hz，2H)、9.42(s，1H)
" synthesizing of exemplary compounds 144 "
Acid chloride 0.16g, tri-butyl phosphine 0.58g are dissolved among the dry toluene 10ml, add sodium borohydride 25mg, after at room temperature stirring 10 minutes, add δ-carboline 2.00g, intermediate a3.20g, sodium tert-butoxide 1.37g, be scattered among the anhydrous dimethyl benzene 50ml, under blanket of nitrogen, under reflux temperature, stirred 10 hours.Put cold after, add chloroform and water, organic layer is separated, after organic layer water, the saturated common salt water washing, decompression concentrates down, with the residue that obtains acetate recrystallization, obtains the colourless crystallization 1.5g of exemplary compounds 144.
The structure of exemplary compounds 144 is used
1H-NMR spectrum and mass spectrum are confirmed.The spectrum data of exemplary compounds 144 are as follows.
MS(FAB)m/z：647(M
+1)
1H-NMR(400MHz，CDCl
3)δ/ppm?1.80(S，12H)、7.27(S，4H)、7.34(dd，J＝4.9Hz，J＝8.3Hz，2H)、7.3-7.4(m，2H)、7.4-7.5(m，12H)、7.76(dd，J＝1.3Hz，J＝8.3Hz、2H)、8.45(d，J＝7.8Hz，2H)、8.63(dd，J＝1.3Hz，J＝4.9Hz，2H)
" synthesizing of exemplary compounds 143 "
With 4,4 '-two chloro-3,3 '-bipyridine 0.85g, diamines b0.59g, dibenzylideneacetonepalladium palladium 44mg, imidazole salts 36mg, sodium tert-butoxide 1.09g add among the dimethoxy-ethane 5ml, heat under 80 ℃ and stirred 24 hours.Put cold back and add chloroform and water, separate organic layer, after organic layer water, the saturated common salt water washing, decompression concentrates down, with the residue that obtains re-crystallizing in ethyl acetate, obtains the colourless crystallization 0.3g of exemplary compounds 143.
The structure of exemplary compounds 143 is used
1H-NMR spectrum and mass spectrum are confirmed.The spectrum data of exemplary compounds 143 are as follows.
MS(FAB)m/z639(M
+1)
1H-NMR(400MHz，CDCl
3)：δ/ppm7.46(d，J＝5.7Hz，4H)、7.6-7.7(m，4H)、7.8-7.9(m，4H)、8.67(d，J＝5.7Hz，4H)、9.51(S，4H)
" synthesizing of exemplary compounds 145 "
In exemplary compounds 143 synthetic, except with 4,4 '-two chloro-3,3 '-pyridine ring of bipyridine changes to benzene and uses beyond 3-(2-chlorphenyl)-4-chloropyridine similarly synthetic exemplary compounds 145.
The structure of exemplary compounds 145 is used
1H-NMR spectrum and mass spectrum are confirmed.The spectrum data of exemplary compounds 145 are as follows.
MS(FAB)m/z637(M
+1)
1H-NMR(400MHz，CDCl
3)δ/ppm?7.3-7.4(m，2H)、7.6-7.7(m，4H)、7.7-7.8(m，4H)7.8-7.9(m，4H)、8.06(d，J＝5.3Hz，2H)、8.23(d，J＝7.8Hz，2H)、8.56(d，J＝5.3Hz，2H)，8.96(S，2H)
In addition, except above-mentioned synthesis example, azepine carbazole ring or its analog of these compounds can be according to J.Chem.Soc., Perkin Trans.1,1505-1510 (1999), Pol.J.Chem., 54,1585 (1980), (Tetrahedron Lett.41 (2000), 481-484) synthetic method of middle record is synthesized.The azepine carbazole ring that is synthesized or its analog and aromatic rings, heterocycle, alkyl etc. can adopt the known method of Liv Ullmann coupling reaction (ウ Le マ Application カ Star プ リ Application グ), the coupling reaction of using the Pd catalyst, ス ズ キ coupling reaction etc. to the importing of nuclear, linking group.
The molecular weight of related compound is preferably more than 400 among the present invention, more preferably is more than 450, and more preferably more than 600, special preferred molecular weight is more than 800.Thus, can improve glass transition temperature, improve thermal stability, the life-span is further prolonged.
Related compound can constitute the constituent of layer as following organic EL among the present invention, but in the present invention, in the formation layer of organic EL of the present invention, preferably in luminescent layer or electron supplying layer (in electron supplying layer, being used as hole barrier materials), contain compound of the present invention, preferably with compound of the present invention as luminescent layer, special preferably its host compound as luminescent layer is used.But, consider that from the viewpoint of the various rerum naturas of control organic EL other that related compound also can be used for organic EL as required among the present invention constitute layer.
Compound related among the present invention can (be carried on the back irradiation with material at organic EL, the plane screen panel display, lighting source, display element, the electronic photography light source, recording light source, exposure light source, read light source, sign, advertisement, room lighting, optical communication apparatus etc.) etc. purposes, but, also can be used as other purposes, at organic semiconductor laser material (recording light source, exposure light source, read light source, optical communication apparatus, electronic photography is with light source etc.), the electronic photographic sensitizer material, organic tft element material (organic memory element, organic calculation element, the organic switching element), organic Wavelength changing element material, photo-electric conversion element material (solar cell, light-sensitive element etc.) use in etc. the wide field.
Describe the formation layer of organic EL of the present invention below in detail.
Among the present invention, the preferred concrete example that the layer of organic EL constitutes is as follows, but the present invention is not subjected to their qualification.
(i) anode/luminescent layer/electron supplying layer/negative electrode
(ii) anode/hole transporting layer/luminescent layer/electron supplying layer/negative electrode
(iii) anode/hole transporting layer/luminescent layer/hole blocking layer/electron supplying layer/negative electrode
(iv) anode/hole transporting layer/luminescent layer/hole blocking layer/electron supplying layer/cathode buffer layer/negative electrode
(v) anode/anode buffer layer/hole transporting layer/luminescent layer/hole blocking layer/electron supplying layer/cathode buffer layer/negative electrode
" anode "
As the anode in the organic EL, preferred (more than the 4eV) metal that work function is big, alloy, conductive compound and composition thereof used is as electrode substance.As the concrete example of kind electrode material, can list the metal of Au etc.; CuI, indium tin oxide (ITO), SnO
2, ZnO etc. the conductive clear material.In addition, also can use IDIXO (In
2O
3-ZnO) wait to amorphous and can be made into the material of nesa coating.As anode, can adopt the method for evaporation or sputter etc. that these electrode substances are formed film, also can adopt photoetching process to form the pattern of desired shape, perhaps at the situation not high (about more than the 100 μ m), also can when the evaporation of above-mentioned electrode substance or sputter, form pattern by the mask by desired shape to the pattern required precision.In the situation that the light that this anode will be sent takes out, wish transmitance greater than 10%, in addition, as the film resistor of anode preferably below hundreds of Ω/.And then thickness can be selected according to material, but selects in the scope of 10nm～1000nm, preferred 10nm～200nm usually.
" negative electrode "
On the other hand, as negative electrode, use little (4eV the is following) metal (being called electronics injection metal) of work function, alloy, conductive compound and composition thereof as electrode substance.As the concrete example of kind electrode material, can list sodium, sodium-potassium-sodium alloy, magnesium, lithium, magnesium/copper mixture, magnesium/silver-colored mixture, magnesium/aluminium mixture, magnesium/indium mixture, aluminium/aluminium oxide (Al
2O
3) mixture, indium, lithium/aluminium mixture, rare earth metal etc.Wherein, consider from the electronics injection with to the viewpoint of the durability of oxidation etc., preferred electron injection metal and work function value be than the mixture of its big second metal that belongs to stable metal, for example magnesium/silver-colored mixture, magnesium/aluminium mixture, magnesium/indium mixture, aluminium/aluminium oxide (Al
2O
3) mixture, lithium/aluminium mixture, aluminium etc.Negative electrode can adopt the method for evaporation or sputter etc. that these electrode substances are formed film and make.In addition, preferably below hundreds of Ω/, thickness is selected in the scope of 10nm～5 μ m, preferred 50～200nm usually as the film resistor of negative electrode.In addition, in order to make the light transmission that sends,, all help improving its glorious degrees as long as the either party of the male or female of organic EL is transparent or translucent.
In addition, after above-mentioned metal is made negative electrode with the thickness of 1～20nm, be produced on the conductive clear material of being enumerated in the anode explanation more in the above, can make transparent or translucent negative electrode thus, adopt this method can make the element that anode and negative electrode both sides have permeability.
The following describes the employed implanted layer of formation layer as organic EL of the present invention, barrier layer, electron supplying layer etc.
" implanted layer: electron injecting layer, hole injection layer "
Implanted layer is provided with as required, has electron injecting layer and hole injection layer, also may reside between aforesaid anode and luminescent layer or the hole transporting layer and negative electrode and luminescent layer or electron supplying layer between.
Implanted layer is to be used to reduce driving voltage and to improve glorious degrees and be arranged at rete between electrode and the organic layer, the 2nd the compiling in the 2nd chapter " electrode material " (123～166 pages) and be documented of " organic EL and industrialization forefront thereof (November in 1998 エ ヌ on the 30th テ イ-エ ス society distribution) ", hole injection layer (anode buffer layer) and electron injecting layer (cathode buffer layer) are arranged.
Anode buffer layer (hole injection layer) opens the spy that flat 9-45479 communique, spy are opened flat 9-260062 communique, the spy opens in flat 8-288069 communique etc. and is documented, as concrete example, can to list with the copper phthalocyanine be the phthalocyanine resilient coating of representative, with the vanadium oxide be representative oxide buffer layer, amorphous carbon resilient coating, use the polymeric buffer layer etc. of the electroconductive polymer of polyaniline (aniline green) and polythiophene etc.
Cathode buffer layer (electron injecting layer) opens the spy that flat 6-325871 communique, spy are opened flat 9-17574 communique, the spy opens in flat 10-74586 communique etc. and is documented, and can list particularly with strontium and aluminium etc. to be the metal buffer layer of representative, to be the alkali metal compound resilient coating of representative with the lithium fluoride, to be the alkaline earth metal compound resilient coating of representative with the magnesium fluoride, to be oxide buffer layer of representative etc. with the aluminium oxide.It is very thin film that above-mentioned resilient coating (implanted layer) is wished, though thickness is relevant with material, its thickness is preferably in the scope of 0.1nm～5 μ m.
" barrier layer: hole blocking layer, electronic barrier layer "
As mentioned above, the barrier layer is to be provided with as required except the basic comprising layer of organic compound thin film.Comprise that spy for example opens the hole barrier (complete closed) layer that flat 11-204258 communique, spy are opened flat 11-204359 communique and record in " organic EL and industrialization forefront thereof (November in 1998 エ ヌ on the 30th テ イ-distribution of エ ス society) " 237 pages etc.
Hole blocking layer is electron supplying layer in a broad sense, be to carry the very little hole barrier materials of ability in hole to constitute by a kind of function with conveying electronic and its, by one side conveying electronic one side blocking hole, thereby electronics is improved with the probability that combines again in hole.
The hole blocking layer of organic EL of the present invention is provided with according to adjacent ground connection with luminescent layer.
Among the present invention,, preferably contain compound related in the invention described above as the hole barrier materials of hole blocking layer.Thus, can make the higher organic EL of luminous efficiency.And then, can make the life-span longer.
On the other hand, electronic barrier layer is hole transporting layer in a broad sense, be to have the function of carrying the hole and the very little material of ability of its conveying electronic constitutes by a kind of, on one side by carrying the hole to stop electronics, thereby can make electronics and hole combine the probability raising again.
" luminescent layer "
Among the present invention related luminescent layer be by electrode or electron supplying layer, hole transporting layer injected electrons and hole again in conjunction with and luminous layer, luminous part can be in the layer of luminescent layer, also can be the interface of luminescent layer and adjoining course.
(host compound)
As follows, in the luminescent layer of organic EL of the present invention, preferably contain host compound and phosphorescent compounds (being also referred to as the phosphorescence luminance compound), in the present invention, as host compound, preferably use compound related among above-mentioned the present invention.Thus, can further improve luminous efficiency.In addition, as host compound, also can contain compound related in the invention described above compound in addition.
Herein, related host compound among the present invention is defined as in the compound that contains in luminescent layer, room temperature (25 ℃) down the luminous phosphorescence quantum yield of phosphorescence be lower than 0.01 compound.
And then, also multiple known host compound can be merged and use.By having multiple host compound, can adjust movement of electric charges, thereby can improve the efficient of organic EL.In addition, by using multiple phosphorescent compounds, the mixing of not sharing the same light of sending can be able to be obtained the light of random color thus.By adjusting kind, the doping of phosphorescent compounds, can send the light of white, thereby also can be applied to illumination and back of the body irradiation.
As these known host compounds, preferably not only have cavity conveying energy, electron transport energy, but also can prevent luminous long wavelengthization, and be the compound of high Tg (glass transition temperature).
As the concrete example of known host compound, can list the compound of putting down in writing in the following document.
The spy opens the 2001-257076 communique, the spy opens the 2002-308855 communique, the spy opens the 2001-313179 communique, the spy opens the 2002-319491 communique, the spy opens the 2001-357977 communique, the spy opens the 2002-334786 communique, the spy opens the 2002-8860 communique, the spy opens the 2002-334787 communique, the spy opens the 2002-15871 communique, the spy opens the 2002-334788 communique, the spy opens the 2002-43056 communique, the spy opens the 2002-334789 communique, the spy opens the 2002-75645 communique, the spy opens the 2002-338579 communique, the spy opens the 2002-105445 communique, the spy opens the 2002-343568 communique, the spy opens the 2002-141173 communique, the spy opens the 2002-352957 communique, the spy opens the 2002-203683 communique, the spy opens the 2002-363227 communique, the spy opens the 2002-231453 communique, the spy opens the 2003-3165 communique, the spy opens the 2002-234888 communique, the spy opens the 2003-27048 communique, the spy opens the 2002-255934 communique, the spy opens the 2002-260861 communique, the spy opens the 2002-280183 communique, the spy opens the 2002-299060 communique, the spy opens the 2002-302516 communique, the spy opens the 2002-305083 communique, the spy opens the 2002-305084 communique, the spy opens 2002-308837 communique etc.
In addition, in the luminescent layer,, also can further contain host compound with the very big wavelength of fluorescence as host compound.Under this situation, by make energy by other host compound and phosphorescent compounds to the moving of fluorescence compound, also can obtain the light that sends from other host compounds with the very big wavelength of fluorescence as the electroluminescent of organic EL.As host compound with the very big wavelength of fluorescence, the high compound of fluorescent quantum yield under solution state preferably.Herein, the fluorescent quantum yield is preferably more than 10%, particularly preferably in more than 30%.As the concrete host compound with the very big wavelength of fluorescence, can list coumarin series pigment, pyrans and be pigment, cyanine and be pigment, Network ロ コ ニ ウ system and be pigment, ス Network ア リ ウ system and be pigment, oxo benzanthracene and be pigment, fluorescence prime system pigment, rhodamine is that pigment, pyrans are that pigment, perylene are that pigment, Stilbene are that pigment, polythiophene are pigment etc.The fluorescent quantum yield can be measured according to the method for record in the beam split II of above-mentioned the 4th edition experimental chemistry lecture 7,362 pages (version, ball were apt in 1992).
(phosphorescent compounds (phosphorescence luminance compound))
As the material that uses in the luminescent layer (hereinafter referred to as luminescent material), preferably when containing the aforementioned body compound, also contain phosphorescent compounds.Thus, can make the higher organic EL of luminous efficiency.
Related phosphorescent compounds among the present invention is the compound that can observe by the light that excites triplet to send, and is at room temperature (25 ℃) phosphorescent compound down, is that the phosphorescence quantum yield is the compound more than 0.01 under 25 ℃.The phosphorescence quantum yield is preferably more than 0.1.
Above-mentioned phosphorescence quantum yield can be measured according to the method for record in the beam split II of the 4th edition experimental chemistry lecture 7,398 pages (version, ball were apt in 1992).Phosphorescence quantum yield in the solution can use all kinds of solvents to measure, and the phosphorescent compounds of using among the present invention can measured in the solvent arbitrarily, but its condition is to reach above-mentioned phosphorescence quantum yield.
Principle of luminosity as phosphorescent compounds, can list 2 kinds, a kind of is so-called energy mobile model, promptly, on the host compound of delivery vehicles, cause the combination again of carrier, thereby produce the excited state of host compound, transfer on the phosphorescent compounds, can obtain the light that sends from phosphorescent compounds by making this energy; Another kind is that so-called carrier captures (キ ヤ リ ア ト ラ Star プ) type, that is, phosphorescent compounds becomes a kind of carrier trap, causes the combination again of carrier on the phosphorescent compounds, thereby obtains the light that sends from phosphorescent compounds; But under any situation, the energy that should be lower than the excited state of host compound with the energy of the excited state of phosphorescent compounds is a condition.
Phosphorescent compounds can be selected in the employed known compound to use from the luminescent layer of organic EL aptly.
As the phosphorescent compounds of using among the present invention, the complex based compound that preferably contains the 8th family's metal in the periodic table of elements, more preferably iridic compound, osmium compound or platinum compounds (platinum complex based compound), terres rares complex, wherein iridic compound most preferably.
The concrete example of the phosphorescent compounds of using among the present invention below is shown, but is not subjected to their qualification.These compounds can be according to for example, and the method for record waits synthetic in the Inorg.Chem.40 volume, 1704～1711.
Among the present invention, have no particular limits as the luminous very big wavelength of the phosphorescence of phosphorescent compounds, on the principle, can wait by the substituting group of selecting central metal, part, part the emission wavelength that obtains is changed, the phosphorescence emission wavelength of phosphorescent compounds preferably has the luminous very big wavelength of phosphorescence at 380～480nm wave band.Utilize the organic EL of the organic EL of this pastiness look phosphorescence or the look phosphorescence that turns white, can further improve luminous efficiency.
The illuminant colour of related compound among organic EL of the present invention and the present invention, be by according to " among Fig. 4 .16 that newly organized color science handbook (Japanese color science can be compiled, Tokyo University's publication meeting, 1985) is the 108th page, the result and the corresponding color of cie color coordinate of dividing light emission brightness photometer CS-1000 (ミ ノ Le system) to record decide.
The formation method of luminescent layer is that for example adopting, known filming methods such as vacuum vapour deposition, method of spin coating, The tape casting, LB method, ink-jet method form above-claimed cpd system film.Thickness as luminescent layer has no particular limits, usually at 5nm～5 μ m, preferably select in the scope at 5nm～200nm.This luminescent layer can be one deck structure that is made of more than a kind or 2 kinds these phosphorescent compounds and host compound, perhaps the lamination structure that also can be made of the multilayer that same composition or difference are formed.
" hole transporting layer "
Hole transporting layer is to be made of the hole transporting material with the function of carrying the hole, and in a broad sense, hole injection layer, electronic barrier layer are also contained in the hole transporting layer.Hole transporting layer can be provided with single or multiple lift.
As hole transporting material, being meant that those have the hole injects or conveying capacity, to the material that electronics has any performance of blocking capability, can be in organic substance, the inorganic matter any.For example, triazole derivative, oxadiazole derivative, imdazole derivatives, polyaryl alkane derivative, pyrazoline derivative and pyrazolone derivative, phenylenediamine derivative, arylamine derivative, amino chalcone derivative, oxazole derivative, styryl anthracene derivant, fluorenone derivatives, hydazone derivative, stilbene derivative, silazane derivative, the aniline based copolymer of replacing can be listed, also electroconductive polymer oligomer, particularly thiophene oligomers etc. can be listed in addition.
As hole transporting material, can use above-mentioned compound, preferably use porphyrin compound, aromatic uncle amine compound and styryl amines, special optimization aromatic tertiary amine compound.
Typical example as aromatic uncle amine compound and styryl amines can list N, N, N ', N '-tetraphenyl-4,4 '-diaminobenzene; N, N '-diphenyl-N, N '-two (3-aminomethyl phenyl)-(1,1 '-biphenyl)-4,4 '-diamines (TPD); 2, two (the 4-di-p-tolyl aminophenyl) propane of 2-; 1, two (the 4-di-p-tolyl aminophenyl) cyclohexanes of 1-; N, N, N ', N '-four p-methylphenyl-4,4 '-benzidine; 1, two (4-di-p-tolyl the aminophenyl)-4-cyclohexylbenzenes of 1-; Two (4-dimethylamino-2-aminomethyl phenyl) phenylmethane; Two (4-di-p-tolyl aminophenyl) phenylmethane; N, N '-diphenyl-N, N '-two (4-methoxyphenyl)-4,4 '-benzidine; N, N, N ', N '-tetraphenyl-4,4 '-diamino-diphenyl ether; 4,4 '-two (diphenylamino) connection four benzene; N, N, N-three (p-methylphenyl) amine; 4-(di-p-tolyl amino)-4 '-(4-(two-p-tolyl amino) styryl) Stilbene; 4-N, N-diphenylamino-(2-diphenylacetylene) benzene; 3-methoxyl group-4 '-N, N-diphenylamino Stilbene; The N-phenyl carbazole; And then, also can enumerate United States Patent (USP) the 5th, 061, have 2 compounds that condense aromatic ring in the molecule of putting down in writing in No. 569 specifications, for example 4,4 '-two (N-(1-naphthyl)-N-phenylamino) biphenyl (NPD), spy open that the star that three triphenylamine unit are arranged (ス -バ-ス ト type) put down in writing in the flat 4-308688 communique is formed by connecting 4,4 ', 4 " three (N-(3-aminomethyl phenyl)-N-phenylamino) triphenylamines (MTDATA) etc.
And then, also can use the macromolecular material that imports in the macromolecular chain or form as high polymer main chain by these materials by these materials.In addition, the inorganic compound of p type-Si, p type-SiC etc. also can be used as hole-injecting material, hole transporting material.
Hole transporting layer for example can adopt, and the known method of vacuum vapour deposition, method of spin coating, The tape casting, the print process that comprises ink-jet method, LB method etc. forms above-mentioned hole transporting material filming.Thickness for hole transporting layer has no particular limits, but is generally about 5nm～5 μ m, is preferably 5～200nm.This hole transporting layer can be by one deck structure that constitutes more than a kind or 2 kinds in the above-mentioned material.
" electron supplying layer "
Electron supplying layer is to constitute by having the conveying electronic materials with function, and in a broad sense, electron injecting layer, hole blocking layer are also contained in the electron supplying layer.Electron supplying layer can be set to single or multiple lift.
Past, electron supplying layer at individual layer, and the situation of making multilayer, as the electron transport materials that uses in the electron supplying layer with respect to luminescent layer and cathode side adjacency (the double hole barrier materials of doing), can be as long as have the function that is delivered to luminescent layer by the negative electrode injected electrons, as this material, can selecting arbitrarily from known compound in the past, compound uses, for example can list nitro substituted fluorene derivative, the diphenyl quinone derivative, titanium dioxide thiapyran derivative, carbodiimides, fluorenylidene (Off レ オ レ ニ リ デ Application) methane Derivatives, anthraquinonyl bismethane and anthracyclinone derivatives oxadiazole derivative etc.And then ， is substituted by sulphur atom Jiang the oxygen atom of oxadiazole ring and the thiadiazoles derivative that forms, knownly has quinoxaline ring and can be used as electron transport materials as the quinoxaline derivant of electron attractive group in Shang Shu oxadiazole derivative.
And then, also can use the macromolecular material that imports in the macromolecular chain or form as high polymer main chain by these materials by these materials.
In addition, the metal complex of oxine derivative, three (oxine) aluminium (Alq for example
3), three (5, the 7-dichloro-8-hydroxyquinoline) aluminium, three (5, the 7-dibromc-8-hydroxyquinoline) aluminium, three (2-methyl-oxine) aluminium, three (5-methyl-oxine) aluminium, two (oxine) zinc (Znq
2) wait and metal complex that their central metal of metal complex replaces with In, Mg, Cu, Ca, Sn, Ga or Pb also can be used as electron transport materials.In addition, no metal or metal phthalocyanine or its end also can be preferably used as electron transport materials by the compound of replacements such as alkyl or sulfonic group.In addition, also can be used as electron transport materials as the illustrative diphenylethyllene pyrazines derivatives of luminescent layer material, same with hole injection layer, hole transporting layer, the inorganic semiconductor of n type-Si, n type-SiC etc. also can be used as electron transport materials.
Electron supplying layer for example can adopt, and the known method of vacuum vapour deposition, method of spin coating, The tape casting, the print process that comprises ink-jet method, LB method etc. forms above-mentioned electron transport materials filming.The thickness of electron supplying layer has no particular limits, and is generally about 5nm～5 μ m, is preferably 5～200nm.Electron supplying layer can be by one deck structure that constitutes more than a kind or 2 kinds in the above-mentioned material.
" matrix "
Organic EL of the present invention preferably forms on matrix.
As the matrix that can be used for organic EL of the present invention (below be also referred to as substrate, base material, support etc.), be not defined in kinds such as glass, plastics especially, and, so long as transparent just having no particular limits, as the substrate of preferred use, can list for example glass, quartz, photopermeability resin film.Particularly preferred matrix is to give flexible resin film to organic EL.
As resin film, for example can list the film that constitutes by PETG (PET), PEN (PEN), polyether sulfone (PES), Polyetherimide, polyether-ether-ketone, polyphenylene sulfide, polyaryl thing, polyimides, Merlon (PC), cellulose triacetate (TAC), cellulose acetate-propionate (CAP) etc. etc.On the surface of resin film, also can form inorganic matter, organic tunicle or its both mixing tunicle.
The luminous efficient that at room temperature is fetched into the outside of organic electroluminescent device of the present invention is preferably more than 1%, more preferably more than 5%.Be fetched into outside quantum efficiency (%)=herein, in the outside luminous number of photons of organic EL/flow into electron number * 100 of organic EL.
In addition, can be simultaneously and with the tone improvement filter disc of colour filter etc. etc., also can be simultaneously and with a kind of variable color filter disc that utilizes fluorophor the color transition of the light that sends from organic EL to be become polychrome.In the situation of using the variable color filter disc, the luminous λ max of organic EL is preferably below the 480nm.
" manufacture method of organic EL "
As an example of organic EL manufacture method of the present invention, the facture of the organic EL that is made of anode/hole injection layer/hole transporting layer/luminescent layer/electron supplying layer/electron injecting layer/negative electrode is described below.
At first, on suitable matrix, adopt the method for evaporation or sputter etc., form the film that constitutes with material by desirable electrode substance, for example anode, make thickness be below the 1 μ m, be preferably 10～200nm, make anode thus.And then form the organic compound thin film of the hole injection layer belong to the organic EL material, hole transporting layer, luminescent layer, electron supplying layer, electron injecting layer, hole blocking layer more in the above.
Filming method as this organic compound thin film, as mentioned above, vapour deposition method, wet processing are arranged (for example, method of spin coating, The tape casting, ink-jet method, print process) etc., but the homogeneous membrane and being difficult to of being easy to get calmly generates the viewpoint of pin hole etc. considers preferred especially vacuum vapour deposition, method of spin coating, ink-jet method, print process.And then, can also adopt every layer of different system embrane method.In the situation that adopts evaporation legal system film, its evaporation condition usually, is wished 50～450 ℃ of heating-up temperatures, vacuum degree 10 on heating plate according to the difference of the kind of employed compound etc. and different
-6～10
-2The suitable selection in the scope of Pa, evaporation rate 0.01～50nm/ second, substrate temperature-50～300 ℃, thickness 0.1nm～5 μ m, preferred 5～200nm.
After these layers form, adopt the method for for example evaporation or sputter etc., form in the above by negative electrode with the film that material constitutes, make thickness, form negative electrode thus, thereby obtain desirable organic EL below the 1 μ m, preferably in the scope at 50～200nm.The making of this organic EL preferably once vacuumizes and forms hole injection layer from start to finish until negative electrode, still, also can take out in manufacturing process, implements different system embrane methods.At this moment, must consider under dry inert gas atmosphere, to carry out operation etc.
The display unit of the present invention of polychrome only is provided with shadow mask when luminescent layer forms, and other layers are common, therefore do not need the pattern of shadow mask etc. to form thing, can adopt vapour deposition method, The tape casting, method of spin coating, ink-jet method, print process etc. on one side, to form film.
When the situation that the pattern that only carries out luminescent layer forms, its method is unqualified, is preferably vapour deposition method, ink-jet method, print process.In the situation that adopts vapour deposition method, preferably use the pattern of shadow mask to form.
And, production order is put upside down, promptly make also being fine according to the order of negative electrode, electron injecting layer, electron supplying layer, luminescent layer, hole transporting layer, hole injection layer, anode.Apply the situation of direct voltage in display unit to the polychrome that obtains like this, with anode be+, with negative electrode for-, apply voltage about 2～40V to form polarity to it, promptly can observe luminous.In addition, also can apply alternating voltage.In addition, the AC wave shape that is applied can be arbitrarily.
Display unit of the present invention can be used as display device, display, various illuminating source.In display device, display, send the organic EL of green grass or young crops, red, green 3 kinds of light by use, can carry out panchromatic demonstration.
As display device, display, can list television set, PC, モ バ イ Le equipment, AV equipment, literal and broadcast information demonstration in demonstration, the automobile etc.The display unit that particularly can be used as regeneration rest image or dynamic image is used, in the situation of the display unit that is used as dynamic image regeneration usefulness, its type of drive can be any mode in simple matrix (パ Star シ Block matrix) mode and active matrix (the ア Network テ イ Block マ ト リ Star Network ス) mode.
As lighting device, can list back of the body irradiation that home-use illumination, room light, clock and watch and liquid crystal use, billboard advertisement, semaphore, the light source of light memory media, the light source of electrophotographic copier, the light source of optical communication processor, light source of light-sensitive element etc., but unqualified to this.
In addition, organic EL of the present invention also can be used as the organic EL use with resonator structure.
As this application target with organic EL of resonator structure, can enumerate the light source of bright dipping memory media, the light source of electrophotographic copier, the light source of optical communication processor, the light source of light-sensitive element etc., unqualified to this.In addition, by making its laser generation, also can be used for such use.
Organic EL Material of the present invention as lighting device, can be used in fact sending the organic EL of white light.Utilize multiple luminescent material to make its light that sends multiple color simultaneously,, can obtain the light of white by colour mixture.As the combination of multiple illuminant colour, can be the combination that contains 3 kinds of luminous very big wavelength of cyan, green, cyan 3 primary colors, also can be the combination that contains cyan and yellow, dark green and orange etc. 2 kinds of luminous very big wavelength that utilize the complementary color relation.
In addition, the combination of luminescent material being carried out as being used to obtain multiple illuminant colour, can be to phosphoresce or the luminescent material of fluorescence carries out multiple combination by multiple, and by the luminescent material that can send fluorescence or phosphorescence and the light that can make self-luminescent material as exciting light and any combination in the combination of luminous dye material, but, in the said white organic electroluminescent element of the present invention, only need light-emitting dopant is carried out multiple combination and mix getting final product.Mask just is set when forming luminescent layer or hole transporting layer or electron supplying layer etc., when utilizing mask to be coated with respectively etc., only need merely dispose mask gets final product, and other layer is common, therefore do not need the pattern of mask etc. to form, can adopt vapour deposition method, The tape casting, method of spin coating, ink-jet method, print process etc. on one side, to form for example electrode film, can also boost productivity like this.According to this method, can be so that with different by the white organic El device that array-like disposes side by side by the light-emitting component of multiple color, element itself just can send the light of white.
Have no particular limits as the luminescent material that uses in the luminescent layer, for example, if the back of the body irradiation in the liquid crystal display cells, in order to be suitable for and the corresponding wave-length coverage of CF (colour filter) characteristic, can from virgin metalization (オ Le ト メ Leization) complex (Ir complex, Pt complex etc.) and known luminescent material, select any luminescent material to make up, thereby can reach whitening.
Like this, related white light emission organic EL among the present invention, except above-mentioned display device, display, can also be as various illuminating sources, lighting device, a kind of lamp in home-use illumination, room light or the exposure light source etc. uses, the display unit that also can be used in addition, the back of the body irradiation etc. of liquid crystal indicator.
In addition, can also enumerate the light source of backlight, the billboard advertisement, semaphore, light memory media etc. of clock and watch etc., the light source of electrophotographic copier, the light source of optical communication processor, the light source of light-sensitive element etc., and the purposes that needs the wide scopes such as general Household Electrical utensil of display unit.
" display unit "
Organic EL of the present invention, a kind of lamp can be used as illumination usefulness or exposure light source etc. uses, and the display unit (display) that also can be used as projection arrangement, direct viewing rest image and the dynamic image type of projected image type is used.In the situation of the display unit that is used as dynamic image regeneration usefulness, its type of drive can be any of simple matrix (passive matrix) mode or active matrix mode.Perhaps, by using the organic EL of the present invention that has different colors more than 3 kinds, can make full color display.Perhaps, illuminant colour of the same colour, for example also can make white light become panchromaticization by use colour filter in BGR.And then, by using the variable color colour filter, also can make the illuminant colour of organic EL change other color into and reach panchromaticization, but in this situation, the luminous λ max of organic EL is preferably below the 480nm.
The following display unit that constitutes by organic EL of the present invention with reference to description of drawings one example.
Fig. 1 is the ideograph that the display unit that an example is made of organic EL is shown.Be the luminous demonstration of carrying out image information by organic EL, for example, the ideograph of the display of portable phone etc.
Display 1 is by the display part A with many pixels, come control part B that the image to display part A scans etc. to constitute according to image information.
Control part B realizes being electrically connected with display part A, according to from the image information of outside transmission sweep signal one by one and viewdata signal to many pixels, pass through sweep signal, make each pixel of scan line luminous in turn and carry out image scanning corresponding to viewdata signal, thereby in display part A displays image information.
The 2nd figure is the ideograph of display part A.
Display part A has the wiring part that comprises multi-strip scanning line 5 and data wire 6 on substrate, and many pixels 3 etc.Critical piece to display part A describes below.The situation that the light that sent by pixel 3 takes out along the direction (following direction) of hollow arrow has been shown among Fig. 2.
The scan line 5 of wiring part and many data wire 6 each free electric conducting material are made, and scan line 5 and data wire 6 intersect vertically by clathrate, are connected with pixel 3 in the position that intersects vertically (details is not shown in the drawings).
The following describes the luminescence process of pixel.
Fig. 3 is the ideograph of pixel.
Pixel has organic EL 10, switching transistor 11, driving transistors 12, capacitor 13 etc.In many pixels, as organic EL 10, can use redness, green, the luminous organic EL of cyan, by with these pixels and place on the same substrate, can carry out panchromatic demonstration.
In Fig. 3, apply viewdata signal by data wire 6 to the drain electrode (De レ イ Application) of switching transistor 11 by control part B.In addition, (ゲ-ト) apply sweep signal, switching transistor 11 begins to drive, thereby makes the viewdata signal that is applied to drain electrode be delivered to the control utmost point of capacitor 13 and driving transistors 12 to the control utmost point of switching transistor 11 by scan line 5 by control part B.
By the transmission of viewdata signal, capacitor 13 charges according to the current potential of viewdata signal, and simultaneously, driving transistors 12 begins to drive.Driving transistors 12, its drain electrode is connected with power line 7, its source electrode (ソ-ス) electrode with organic EL 10 is connected, according to the current potential of viewdata signal that puts on the control utmost point, by power line 7 to organic EL 10 supplying electric currents.
By the sequential scanning of control part B, sweep signal is transferred to the scan line 5 of next stage, and switching transistor 11 begins to drive immediately.Yet, even switching transistor 11 is in driving condition, capacitor 13 still can keep the current potential of the viewdata signal that charged, thereby the driving condition of driving transistors 12 is remained to the moment that next time applies sweep signal always, thereby it is luminous that organic EL 10 is continued.When applying sweep signal one by one, drive above-mentioned driving transistors 12 according to current potential, thereby make organic EL 10 luminous with the viewdata signal of the sweep signal number of times same period by sequential scanning.
The luminous of organic EL 10 undertaken by following manner,, with respect to many pixels organic EL 10 separately, is provided as the switching transistor 11 and the driving transistors 12 of active element that is, makes many pixels 3 organic EL 10 separately luminous thus.So luminescent method is called the active matrix mode.
Herein, organic EL 10 luminous, can be the light of a plurality of grades of sending of many-valued viewdata signal that the current potential according to a plurality of grades that keep produces, also can make luminous quantity instruct it luminous or not luminous according to the viewdata signal defined of 2 values.
In addition, the current potential of capacitor 13 can continue to remain to the moment that next time applies sweep signal, also can discharge before applying sweep signal being next to next time.
Among the present invention, be not limited to above-mentioned active matrix mode, also can be sweep signal only the data-signal when being scanned make the light emitting drive of the luminous passive matrix mode of organic EL.
Fig. 4 is the ideograph according to the display unit of passive matrix mode.In Fig. 4, multi-strip scanning line 5 clips pixel 3 subtends ground by the clathrate setting with multiple bar chart as data wire 6.
Utilize when scanning applies the sweep signal of scan line 5 successively, the pixel 3 that links to each other with the scan line 5 that is applied is luminous corresponding to viewdata signal.In the passive matrix mode, in pixel 3, do not have active element, manufacturing cost is reduced.
Below, by embodiment the present invention is described, but embodiment of the present invention are not subjected to the qualification of these embodiment.
Embodiment 1
" making of organic EL 1-1～1-23 "
As anode, having made thickness on the glass substrate of 100mm * 100mm * 1.1mm is the last pattern circuit that forms of substrate (the system NA45 of NH テ Network ノ グ ラ ス society) of ITO (indium tin oxide) film of 100nm, then, the transparent support substrate that is provided with this ito transparent electrode is carried out ultrasonic washing in isopropyl alcohol, dry with the drying nitrogen soma, carried out the UV ozone washing 5 minutes.This transparent support substrate is fixed on the substrate fixture of commercially available vacuum deposition apparatus, on the other hand, on molybdenum system resistance heating plate, place α-NPD 200mg, on another molybdenum system resistance heating plate, place exemplary compounds 9 200mg as host compound, on another molybdenum system resistance heating plate, place バ ソ キ ユ プ ロ イ Application (BCP) 200mg, on another molybdenum system resistance heating plate, place Ir-12100mg, and on another molybdenum system resistance heating plate, place Alq
3200mg attaches it in the vacuum deposition apparatus then.
Secondly, vacuum tank is decompressed to 4 * 10
-4Behind the Pa,, heat, to transparent support substrate, the 1st hole transporting layer is set so with the evaporation rate evaporation of 0.1nm/ second to the above-mentioned heating plate energising that is placed with α-NPD.And then, to the above-mentioned heating plate energising that is placed with exemplary compounds 9 and Ir-12, heat, respectively with the evaporation rate of 0.2nm/ second, 0.012nm/ second altogether evaporation to above-mentioned the 1st hole transporting layer, luminescent layer is set thus.In addition, the substrate temperature during evaporation is a room temperature.And then, to the above-mentioned heating plate energising that is placed with BCP, heat, to above-mentioned luminescent layer, the hole blocking layer of thickness 10nm is set so with the evaporation rate evaporation of 0.1nm/ second.On this basis, and then, to being placed with Alq
3The energising of above-mentioned heating plate, heat, to above-mentioned hole blocking layer, the electron supplying layer of thickness 40nm is set with the evaporation rate evaporation of 0.1nm/ second again.In addition, the substrate temperature during evaporation is a room temperature.
Then, evaporation lithium fluoride 0.5nm and aluminium 110nm form negative electrode, make organic EL 1-1 thus.
In the making of organic EL 1-1, the exemplary compounds 9 that to use as the host compound of luminescent layer replaces with each compound shown in the table 1, except that host compound, make organic EL 1-2～1-21 according to the method identical with organic EL 1-1.Below the structure of the compound of above-mentioned use is shown in.
" evaluation of organic EL 1-1～1-21 "
Following such organic EL 1-1～1-21 that estimates made.
(briliancy)
Use is obtained briliancy (cd/m by the briliancy that a minute light emission brightness photometer CS-1000 (コ ニ カ ミ ノ Le セ Application シ Application グ society system) records
2).
(the outside quantum efficiency of taking out)
For the organic EL of made, be determined under 23 ℃, dry nitrogen gas atmosphere and apply 2.5mA/cm
2Constant current the time the outside take out quantum efficiency (%).In addition, during mensuration, use identical branch light emission brightness photometer CS-1000 (コ ニ カ ミ ノ Le セ Application シ Application グ society system).
The briliancy of putting down in writing in the following table, outside measurement result of taking out quantum efficiency are represented as 100 o'clock relative value with the measured value of organic EL 1-15.
With above the results are shown in the following table of obtaining.
The result who puts down in writing from above-mentioned table compares with comparative example as can be seen, the briliancy height of organic EL of the present invention, and also the outside quantum efficiency of taking out is very good.
Embodiment 2
" making of organic EL 2-1～2-20 "
As anode, having made thickness on the glass substrate of 100mm * 100mm * 1.1mm is the last pattern circuit that forms of substrate (the system NA45 of NH テ Network ノ グ ラ ス society) of ITO (indium tin oxide) film of 100nm, then, the transparent support substrate that is provided with this ito transparent electrode is carried out ultrasonic washing in isopropyl alcohol, dry with the drying nitrogen soma, carried out the UV ozone washing 5 minutes.This transparent support substrate is fixed on the substrate fixture of commercially available vacuum deposition apparatus, on the other hand, on molybdenum system resistance heating plate, place α-NPD 200mg, on another molybdenum system resistance heating plate, place CBP 200mg, on another molybdenum system resistance heating plate, place exemplary compounds 9200mg as hole barrier materials, on another molybdenum system resistance heating plate, place Ir-1100mg, and on another molybdenum system resistance heating plate, place Alq
3200mg attaches it in the vacuum deposition apparatus then.
Secondly, vacuum tank is decompressed to 4 * 10
-4Behind the Pa,, heat, to transparent support substrate, first hole transporting layer is set so with the evaporation rate evaporation of 0.1nm/ second to the above-mentioned heating plate energising that is placed with α-NPD.And then, to the above-mentioned heating plate energising that is placed with CBP and Ir-1, heat, respectively with the evaporation rate of 0.2nm/ second, 0.012nm/ second altogether evaporation to above-mentioned hole transporting layer, luminescent layer is set so.In addition, the substrate temperature during evaporation is a room temperature.And then, to the above-mentioned heating plate energising that is placed with exemplary compounds 9, heat, to above-mentioned luminescent layer, the hole blocking layer of thickness 10nm is set so with the evaporation rate evaporation of 0.1nm/ second.On this basis, and then, to being placed with Alq
3The energising of above-mentioned heating plate, heat, to above-mentioned hole blocking layer, the electron supplying layer of thickness 40nm is set with the evaporation rate evaporation of 0.1nm/ second again.In addition, the substrate temperature during evaporation is a room temperature.
Then, evaporation lithium fluoride 0.5nm and aluminium 110nm form negative electrode, make organic EL 2-1 thus.
In the making of organic EL 2-1, will replace with the compound shown in the following table as the exemplary compounds 9 that hole barrier materials uses, in addition, make 2-1～2-20 according to the method identical with organic EL 2-1.
" evaluation of organic EL 2-1～2-20 "
Estimate the briliancy of organic EL 2-1～2-20, the outside quantum efficiency of taking out similarly to Example 1.And then, estimate the life-span according to the determination method shown in following.
(life-span)
When with 2.5mA/cm
2Constant current driven the time, measure briliancy and be reduced to the needed time of a half that is next to the briliancy (initial stage briliancy) after the luminous beginning, with it as partly subtracting life time (τ 0.5), with this as index of aging.In addition, use during mensuration and divide a light emission brightness photometer CS-1000 (コ ニ カ ミ ノ Le セ Application シ Application グ society system).
What more than obtain the results are shown in the following table.In addition, the briliancy of putting down in writing in the following table, outside taking-up quantum efficiency and the measurement result in life-span are represented as 100 o'clock relative value with organic EL 2-12.
The organic EL hole stops the outside life-span remarks that take out of briliancy
Numbering material quantum efficiency
2-1 9 120 120 325 the present invention
2-2 11 130 129 534 the present invention
2-3 15 125 123 330 the present invention
2-4 16 120 122 357 the present invention
2-5 23 105 103 296 the present invention
2-6 40 122 120 440 the present invention
2-7 50 125 126 600 the present invention
2-8 53 110 112 320 the present invention
2-9 56 124 122 764 the present invention
2-10 79 106 105 250 the present invention
2-11 88 103 102 305 the present invention
2-12 BCP 100 100 100 comparative examples
2-13 73 118 118 621 the present invention
2-14 74 114 115 832 the present invention
2-15 105 120 120 537 the present invention
2-16 119 115 114 945 the present invention
2-17 123 112 111 584 the present invention
2-18 131 110 110 482 the present invention
2-19 132 113 112 561 the present invention
2-20 140 121 123 556 the present invention
The result who puts down in writing from last table compares with comparative example as can be seen, the briliancy height of organic EL of the present invention, and the outside quantum efficiency of taking out is good, and reaches life-span lengthization.
" making of organic EL 3-1～3-8 "
In the making of the organic EL 1-1 that in embodiment 1, puts down in writing, the host compound of luminescent layer is changed to the compound of putting down in writing in the following table, Ir-12 is changed to Ir-1, and then BCP is changed to B-Alq, in addition, similarly make organic EL 3-1～3-8.
" evaluation of organic EL 3-1～3-8 "
Estimate the briliancy of organic EL 3-1～3-8, the outside quantum efficiency of taking out similarly to Example 1.And then, estimate keeping quality according to the determination method shown in following.
(keeping quality)
Preservation is after 24 hours down at 85 ℃ with each organic EL, and mensuration is preserved front and back with 2.5mA/cm
2Constant current driven the time each briliancy, obtain each luminance ratio according to following formula, with it as conservatory yardstick.
Briliancy (2.5mA/cm after keeping quality (%)=preservation
2Briliancy (2.5mA/cm before)/preserve
2) * 100
What more than obtain the results are shown in the following table.
The result who puts down in writing from last table compares with comparative example as can be seen, the briliancy height of organic EL of the present invention, and the outside quantum efficiency of taking out is good, and keeping quality is good.Wherein, particularly preferably being compound, especially molecular weight by general formula (1-12) expression is compound more than 450.
Embodiment 4
" making of organic EL 4-1～4-8 "
In the making of the organic EL 1-1 that in embodiment 1, puts down in writing, the host compound of luminescent layer is changed to the compound of putting down in writing in the following table, Ir-12 is changed to Ir-1, and then BCP is changed to B-Alq, in addition, similarly make organic EL 4-1～4-8.
" evaluation of organic EL 4-1～4-8 "
Estimate the briliancy of organic EL 4-1～4-8, the outside quantum efficiency of taking out similarly to Example 1.And then, estimate 50 ℃ of driving life-spans according to the determination method shown in following.
(50 ℃ drive the life-span)
With each organic EL under 50 ℃ certain condition, to give initial stage briliancy 1000cd/m
2Electric current carry out constant current driven, obtain the 1/2 (500cd/m that reaches the initial stage briliancy
2) time, with it as 50 ℃ of yardsticks that drive the life-spans.In addition, 50 ℃ of driving life-spans are represented as 100 o'clock relative value with organic EL 4-6 relatively.
What more than obtain the results are shown in the following table.
The result who puts down in writing from last table compares with comparative example as can be seen, the briliancy height of organic EL of the present invention, and the outside quantum efficiency of taking out is good, and 50 ℃ of driving life-spans are good.Wherein, particularly preferably being compound, especially molecular weight by general formula (1-13) expression is compound more than 450.
" making of organic EL 5-1～5-8 "
In the making of the organic EL 1-1 that in embodiment 1, puts down in writing, the host compound of luminescent layer is changed to the compound of putting down in writing in the following table, Ir-12 is changed to Ir-1, and then BCP is changed to B-Alq, in addition, similarly make organic EL 5-1～5-8.
" evaluation of organic EL 5-1～5-8 "
Estimate the briliancy of organic EL 5-1～5-8, the outside quantum efficiency of taking out similarly to Example 1.And then, estimate the life-span at initial stage according to the determination method shown in following.
(life-span at initial stage)
With each organic EL to give initial stage briliancy 1000cd/m
2Electric current carry out constant current driven, obtain briliancy and reach 90% (900cd/m
2) time, with its yardstick as the life-span at initial stage.In addition, the life-span at initial stage is represented as 100 o'clock relative value with organic EL 5-6 relatively.
What more than obtain the results are shown in the following table.
The result who puts down in writing from last table compares with comparative example as can be seen, the briliancy height of organic EL of the present invention, and the outside quantum efficiency of taking out is good, and the life-span at initial stage is good.Wherein, good especially by the compound of general formula (1-11) expression.
" making of organic EL 6-1～6-8 "
In the making of the organic EL 1-1 that in embodiment 1, puts down in writing, the host compound of luminescent layer is changed to the compound of putting down in writing in the following table, Ir-12 is changed to Ir-1, and then BCP is changed to B-Alq, in addition, similarly make organic EL 6-1～6-8.
" evaluation of organic EL 6-1～6-8 "
Estimate the briliancy of organic EL 6-1～6-8, the outside quantum efficiency of taking out similarly to Example 1.And then, estimate driving voltage according to the determination method shown in following.
(driving voltage)
So-called driving voltage is meant with 2.5mA/cm
2Voltage during driving is obtained poor with the driving voltage (V) of relatively organic EL 6-6.
The driving voltage (V) of driving voltage (V)-organic EL of the present invention of driving voltage (V)=organic EL 6-6
What more than obtain the results are shown in the following table.
The result who puts down in writing from last table compares with comparative example as can be seen, the briliancy height of organic EL of the present invention, and the outside quantum efficiency of taking out is good, and driving voltage is good.Wherein, good especially by the compound of general formula (1-1)～(1-4) expression.
" making of organic EL 7-1～7-8 "
In the making of the organic EL 2-12 that in embodiment 2, puts down in writing, the host compound (CBP) of luminescent layer is changed to exemplary compounds 130, and then the BCP of hole blocking layer changed to the hole barrier materials of putting down in writing in the following table, in addition, similarly make organic EL 7-1～7-8.
" evaluation of organic EL 7-1～7-8 "
Estimate the keeping quality of organic EL 7-1～7-8 similarly to Example 3, what obtain the results are shown in the following table.
The result who puts down in writing from last table compares with comparative example as can be seen, the briliancy height of organic EL of the present invention, and the outside quantum efficiency of taking out is good, and keeping quality is good.Wherein, particularly preferably being compound, especially molecular weight by general formula (1-12) expression is compound more than 450.
Embodiment 8
" making of organic EL 8-1～8-8 "
In the making of the organic EL 2-12 that in embodiment 2, puts down in writing, the host compound (CBP) of luminescent layer is changed to exemplary compounds 130, and then the BCP of hole blocking layer changed to the hole barrier materials of putting down in writing in the following table, in addition, similarly make organic EL 8-1～8-8.
" evaluation of organic EL 8-1～8-8 "
Estimate the briliancy of organic EL 8-1～8-8, the outside taking-up quantum efficiency and 50 ℃ of driving life-spans similarly to Example 4, what obtain the results are shown in the following table.
In addition, 50 ℃ of measurement results that drive the life-span putting down in writing in the following table are represented as 100 o'clock relative value with organic EL 8-6.
The result who puts down in writing from last table compares with comparative example as can be seen, the briliancy height of organic EL of the present invention, and the outside quantum efficiency of taking out is good, and 50 ℃ of driving life-spans are good.Wherein, particularly preferably being compound, especially molecular weight by general formula (1-13) expression is compound more than 450.
Embodiment 9
" making of organic EL 9-1～9-8 "
In the making of the organic EL 2-12 that in embodiment 2, puts down in writing, the host compound (CBP) of luminescent layer is changed to exemplary compounds 130, and then the BCP of hole blocking layer changed to the hole barrier materials of putting down in writing in the following table, in addition, similarly make organic EL 9-1～9-8.
" evaluation of organic EL 9-1～9-8 "
Estimate the briliancy of organic EL 9-1～9-8, the outside taking-up quantum efficiency and life-span at initial stage similarly to Example 5, what obtain the results are shown in the following table.
The measurement result in the life-span of putting down in writing in the following table in addition, at initial stage is represented as 100 o'clock relative value with organic EL 9-6.
The result who puts down in writing from last table compares with comparative example as can be seen, the briliancy height of organic EL of the present invention, and the outside quantum efficiency of taking out is good, and the life-span at initial stage is good.Wherein, good especially by the compound of general formula (1-11) expression.
" making of organic EL 10-1～10-8 "
In the making of the organic EL 2-12 that in embodiment 2, puts down in writing, the host compound (CBP) of luminescent layer is changed to exemplary compounds 130, and then the BCP of hole blocking layer changed to the hole barrier materials of putting down in writing in the following table, in addition, similarly make organic EL 10-1～10-8.
" evaluation of organic EL 10-1～10-8 "
Estimate the briliancy of organic EL 10-1～10-8, outside quantum efficiency and the driving voltage of taking out similarly to Example 6, what obtain the results are shown in the following table.
In addition, the driving voltage of putting down in writing in the following table adopts with the difference of organic EL 10-6 and obtains.
The result who puts down in writing from last table compares with comparative example as can be seen, the briliancy height of organic EL of the present invention, and the outside quantum efficiency of taking out is good, and driving voltage is good.Wherein, good especially by the compound of general formula (1-1)～(1-4) expression.
The organic EL 2-7 of the present invention that makes among making organic EL 1-1 of the present invention, the embodiment 2 among the embodiment 1, the phosphorescent compounds of organic EL 2-7 of the present invention are replaced with exemplary compounds Ir-9, in addition, similarly make the emitting red light organic EL, these emitting red light organic ELs are set up in parallel on same substrate, make active matrix mode full color display shown in Figure 1.The ideograph of display part A of the full color display of making only is shown among Fig. 2.Promptly, on same substrate, have wiring part that contains multi-strip scanning line 5 and data wire 6 and a plurality of pixels 3 that are set up in parallel (luminous color is the pixel of red area, the pixel of green area, the pixel in cyan zone etc.), the scan line 5 of wiring part and many data wire 6 each free electric conducting material constitute, scan line 5 is pressed the clathrate square crossing with data wire 6, is connected with pixel 3 in the position of square crossing (details is not shown).Above-mentioned a plurality of pixel 3, corresponding to the organic EL of separately illuminant colour, drive in the active matrix mode that is provided with separately as the switching transistor and the driving transistors of active element, in case apply sweep signal by scan line 5, will receive viewdata signal, carry out luminous according to the view data that is received from data wire 6.Like this, be set up in parallel aptly, just can carry out panchromatic demonstration by the pixel that each is red, green, blue or green.
By driving full color display, can obtain outside take out quantum efficiency height and durability panchromatic dynamic image demonstration good, the image distinctness.
Industrial applicibility
As mentioned above, according to the present invention, can provide a kind of luminous efficiency height, long having of life-span Organic electro luminescent element and display unit.
Claims (6)
1. an organic electroluminescent device is characterized in that, has the formation layer that comprises the phosphorescent luminescent layer at least between pair of electrodes, and the one deck at least in the above-mentioned formation layer contains the compound by following general formula (17) expression,
General formula (17)
In the formula, o, p represent 1～3 integer, Ar separately
1, Ar
2Represent the arlydene of divalent or the aromatic heterocycle of divalent separately, Z
1, Z
2, Z
3, Z
4Expression contains 6 yuan of heteroaromatics of at least one nitrogen-atoms separately, and L represents the linking group of divalent.
2. organic electroluminescent device as claimed in claim 1 is characterized in that, contains the compound by above-mentioned general formula (17) expression in the above-mentioned phosphorescent luminescent layer.
3. organic electroluminescent device as claimed in claim 1 is characterized in that, at least 1 layer in the above-mentioned formation layer is hole blocking layer, contains the compound by above-mentioned general formula (17) expression in the above-mentioned hole blocking layer.
4. the organic electroluminescent device described in wantonly 1 of claim 1～3 is characterized in that, sends the light of cyan.
5. the organic electroluminescent device described in wantonly 1 of claim 1～3 is characterized in that, sends the light of white.
6. a display unit is characterized in that, has the organic electroluminescent device described in wantonly 1 of the claim 1～5.
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| JP2003-117886 | 2003-04-23 | ||
| JP2003117886 | 2003-04-23 | ||
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| CN106810569A (en) * | 2016-07-26 | 2017-06-09 | 浙江华显光电科技有限公司 | A kind of carboline trisubstituted derivative and its application |
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| CN103682169B (en) * | 2013-12-19 | 2016-09-28 | 江西冠能光电材料有限公司 | A kind of bipolar body material |
| CN105111230A (en) * | 2015-09-18 | 2015-12-02 | 武汉尚赛光电科技有限公司 | Di-aza-carbazole derivatives and application thereof |
| US20200006687A1 (en) * | 2017-03-21 | 2020-01-02 | Konica Minolta, Inc. | Organic electroluminescence element |
| CN109422743A (en) * | 2017-08-29 | 2019-03-05 | 武汉尚赛光电科技有限公司 | Miscellaneous carbazole derivates of dinitrogen and preparation method thereof and application as electroluminescent material |
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| GB9623204D0 (en) * | 1996-11-07 | 1997-01-08 | Univ Durham | Polymer light emitting diode |
| JP3820752B2 (en) * | 1998-06-26 | 2006-09-13 | ソニー株式会社 | Organic electroluminescence device |
| EP1067165A3 (en) * | 1999-07-05 | 2001-03-14 | Konica Corporation | Organic electroluminescent element |
| US6458475B1 (en) * | 1999-11-24 | 2002-10-01 | The Trustee Of Princeton University | Organic light emitting diode having a blue phosphorescent molecule as an emitter |
| CN100338172C (en) * | 2002-12-12 | 2007-09-19 | 出光兴产株式会社 | Organic electroluminescent device material and organic electroluminescent device using the same |
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| CN106810569A (en) * | 2016-07-26 | 2017-06-09 | 浙江华显光电科技有限公司 | A kind of carboline trisubstituted derivative and its application |
| CN106810569B (en) * | 2016-07-26 | 2022-07-22 | 浙江华显光电科技有限公司 | Carboline trisubstituted derivative and application thereof |
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| CN101414667B (en) | 2010-06-09 |
| CN101510590A (en) | 2009-08-19 |
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