(19) United States
`(12) Patent Application Publication (10) Pub. N0.: US 2006/0051612 A1
`Ikeda et al.
`(43) Pub. Date:
`Mar. 9, 2006
`
`US 20060051612A1
`
`(54) LIGHT-EMITTING DEVICE, CONDENSED
`POLYCYCLIC COMPOUND UsED THEREIN
`AND METHOD FOR PRODUCING SAME
`
`(76) Inventors: Masaaki Ikeda, Kita-ku (JP); Takaaki
`Kurata, Kita-ku (JP); Teppei Tsuchida,
`Kita-ku (JP); Chihaya Adachi,
`Chitose-shi (JP)
`
`Correspondence Address:
`NIELDS & LEMACK
`176 EAST MAIN STREET, SUITE 7
`WESTBORO, MA 01581 (US)
`
`(21) Appl. No.:
`
`10/542,085
`
`(22) PCT Filed:
`
`Jan. 16,2004
`
`(86) PCT No.:
`
`PCT/JP04/00306
`
`(30)
`
`Foreign Application Priority Data
`
`Jan. 17, 2003 (JP) .................................... .. 2003-009304
`Jun. 11, 2003
`.. 2003-166799
`Jun. 18, 2003
`.. 2003-172896
`Jun. 26, 2003 (JP) .................................... .. 2003-181925
`
`Aug. 28, 2003 (JP) .................................... .. 2003-305338
`Nov. 12, 2003 (JP) .................................... .. 2003-382625
`
`Publication Classi?cation
`
`(51) Int. Cl.
`(2006.01)
`H05B 33/14
`(2006.01)
`C09K 11/06
`(2006.01)
`C07D 493/02
`(2006.01)
`C07D 495/02
`(52) US. Cl. ....................... .. 428/690; 428/917; 313/504,
`313/506; 257/88; 257/102,
`257/103, 257/E51; 257/E51;
`549/381; 549/24
`
`ABSTRACT
`(57)
`The device according to the invention is a device having
`organic thin ?lms containing a light-emitting layer betWeen
`an anode and a cathode that emits light by application of
`electric energy, characterized in that the light-emitting
`device contains at least a compound having the basic skel
`eton represented by the following General Formula (1) or
`(2). Use of the condensed polycyclic compound according to
`the invention alloWs production of high-brightness, high
`ef?ciency light-emitting device superior in color purity.
`
`DUK SAN NEOLUX
`EXHIBIT 1024
`PAGE 000001
`
`

`
`Patent Application Publication Mar. 9, 2006
`
`US 2006/0051612 A1
`
`Figure 1
`
`Figure 2
`
`Cathode
`Electron-transporting layer
`
`Light-emitting layer
`Positive hole-transporting layer
`Anode
`
`Substrate
`
`Cathode
`Electron-transporting layer
`
`Positive hole-transporting layer
`Positive hole-injecting layer
`
`Anode
`Substrate
`
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`

`
`US 2006/0051612 A1
`
`Mar. 9, 2006
`
`LIGHT-EMITTING DEVICE, CONDENSED
`POLYCYCLIC COMPOUND USED THEREIN AND
`METHOD FOR PRODUCING SAME
`
`TECHNICAL FIELD
`
`[0001] The invention relates to a light-emitting device
`having a thin ?lm of organic compound that emits light by
`application of electricity, a condensed polycyclic compound
`for use therein, and the production method thereof. The
`light-emitting devices are usable in various ?elds including
`display device, ?at panel display, backlight, illumination,
`interior goods, sign and mark, signboard, electrophoto
`graphic camera, optical signal generator, and the like.
`
`BACKGROUND ART
`
`[0002] Development of and studies on organic electronic
`parts using organic materials, have been conducted eagerly
`recently. Examples of such parts include organic electronic
`devices such as organic transistor, organic semiconductor
`laser, organic solar battery, and organic EL device. In
`particular, organic EL (electroluminescent) devices, prom
`ising high-quality display devices, are on the verge of
`commercialiZation. The organic EL devices, Which are par
`ticularly loWer in electric consumption and have various
`advantageous characteristics such as ultra-thin ?lm, high
`brightness light emission, and high visibility due to high
`self-luminescence, have been studied and developed inten
`sively as next-generation display, planar light source, light
`emitting device, and the like.
`[0003] In typical con?gurations, the organic EL device
`using organic materials have a tWo-layer structure (single
`hetero structure) having an organic ?uorescent material thin
`?lm (light-emitting layer) and a positive hole-transporting
`layer that are laminated to each other betWeen a cathodic
`metal electrode and an anodic transparent electrode, a three
`layer structure (double hetero structure) having an electron
`transporting layer, a light-emitting layer, and a positive
`hole-transporting layer that are laminated to each other
`betWeen a metal electrode and a transparent electrode, and
`the like. The positive hole-transporting layer has the func
`tions of receiving positive holes from the anode, transport
`ing the positive holes, and blocking electrons, While the
`electron-transporting layer has the functions of receiving
`electrons from the cathode and transporting the electrons. In
`addition, organic EL devices having a multilayer structure
`containing a positive hole-injecting layer, an electron-inject
`ing layer or a positive hole-blocking layer, or the like
`additionally as needed Were also developed. Each of these
`organic EL devices has its oWn unique structure functionally
`specialiZed from those of the organic EL devices having the
`tWo- or three-layer structure, for example, a structure func
`tionally strengthened to receive positive holes or electrons or
`blocking leak electrons or positive holes, or alloWing high
`brightness by more ef?cient recombination of electron and
`positive hole, improvement in durability, elongation of life
`time, or reduction in electric consumption by reduction of
`applied voltage.
`[0004] In such light-emitting devices having organic thin
`?lms, a substrate of glass, plastic or a suitable material is
`placed outside the transparent electrode. Recombination of
`the electrons injected from a metal electrode and the positive
`holes injected from a transparent electrode, for example, of
`
`indium tin oxide (ITO) in the organic material thin ?lm
`betWeen the tWo electrodes generates excitons, Which emit
`light in the process of emission inactivation, and the light is
`emitted outWard via the transparent electrode and the glass
`substrate. Characteristically, these devices are thinner in
`shape and alloW, for example, high-brightness light emission
`at a loWer drive voltage, and multi-color light emission by
`proper choice of the light-emitting material.
`
`[0005] In representative con?guration of the organic lami
`nated thin ?lm light-emitting device proposed by a research
`group in Eastman Kodak Company, a positive hole-trans
`porting layer of diamine compound, light-emitting and also
`electron-transporting layers of tris(8-quinolinolato)alumi
`num complex, and a cathode of MgzAg (alloy) are formed in
`that order on an ITO glass substrate.
`
`[0006] For producing for full-color displays, devices hav
`ing blue, green, and red light-emitting devices coated on a
`substrate separately are noW studied. Among the light
`emitting devices, the green light-emitting material, Which is
`formed by vapor deposition of a loW-molecular Weight
`compound, is higher in maturity and closer to commercial
`iZation, at a level superior in practicality such as brightness
`and durability. HoWever, the red and blue light-emitting
`materials are left delayed in development, and in particular
`in red light-emitting materials, there is a problem that there
`are no such light-emitting materials that are superior in
`durability and shoW sufficient brightness and color purity.
`An orange device relatively higher in ef?ciency Was pre
`pared for production of a multi-colored display, but cur
`rently, the ef?ciency is still insufficient and the material
`expensive. Because of the problem of device deterioration,
`devices emitting White light have also been studied inten
`sively. Even With these White light-emitting materials, there
`is also the problem that there are no materials that are
`superior in durability and shoW suf?cient brightness and
`suf?cient color purity.
`
`[0007] Examples of the red light-emitting materials
`include perylenes such as bis (diisopropylphenyl)perylene,
`porphyrins, europium complexes, julolidine-substituted
`styryl compounds (e.g., Japanese Patent Application Laid
`Open (JP-A) No. 2001-43974), and the like. The emission
`color (emission Wavelength) is adjusted to a desired color
`used by doping method, i.e., by adding a trace amount of red
`?uorescence compound into the host material as a dopant.
`Examples of the host materials include metal complexes of
`quinolinol derivatives such as tris(8-quinolinolato)alumi
`num complex, bis(10-benZoquinolinolato)beryllium com
`plexes, diarylbutadiene derivatives, stilbene derivatives,
`benZoxaZole
`derivatives,
`benZothiaZole
`derivatives,
`perynone derivatives, and the like. Examples of the dopants
`include red ?uorescence compounds such as 4-(dicyanom
`ethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran
`(DCM), metalphthalocyanine compounds (MgPc, AlPcCl,
`etc.), squarylium compounds, coumarin compounds (see
`e.g., JP-A No. 10-060427), violanthrone compounds, nail
`ered, S-cyanopyrromethene-BF4 complexes (see e.g., JP-A
`No. 11-176572); and red emission light is obtained by
`doping the host material With the compound.
`
`[0008] HoWever, among those light-emitting materials
`(host and dopant materials) commonly used in the art, there
`are many light-emitting materials that have inferior lumi
`nous efficiency prohibiting high brightness, have poor color
`
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`
`

`
`US 2006/0051612 A1
`
`Mar. 9, 2006
`
`purity and a pale orange emission light only even When
`doped, or have loW durability and a shortened lifetime of the
`device; thus, there eXists a serious problem that there is no
`material satisfying the requirements in color purity and
`brightness at the same time. In addition, the orange light
`emitting devices are still unsatisfactory in ef?ciency. Fur
`ther, there is currently no White device for use as backlight
`or others that are higher in brightness and in luminous
`ef?ciency, longer in lifetime, and favorable in color purity.
`[0009] In such a light-emitting device, a transparent elec
`trode formed on a glass or polymer substrate is generally
`used as an anode; and a positive hole-injecting layer, a
`positive hole-transporting layer, and others are normally
`formed thereon. These transparent electrodes for eXample of
`ITO generally have a Work function signi?cantly different
`from that of the positive hole-transporting layer, and are
`different in energy level from the positive hole-transporting
`layer and adhesion betWeen the ITO layer and the positive
`hole-transporting layer is poorer, Which occasionally lead to
`crystalliZation of the positive hole-transporting layer and
`decrease in ef?ciency due to higher applied voltage, conse
`quently causing instability during operation. Although a
`method of forming the transparent electrode, for eXample, of
`ITO lastly, similarly to the top emission structure, Was
`studied recently, there Was still the problem of similar
`deterioration in ef?ciency.
`[0010] Examples of the materials for the positive hole
`injecting layer include the phthalocyanine derivatives
`described in JP-A Nos. 57-51781, 63-295695and8-199161;
`the loW-molecular Weight compounds such as thiophene
`derivatives (see JP-A No. 5-94877), aromatic amine deriva
`tives (see JP-A No. 8-269445), hydraZone derivatives (see
`JP-A No. 4-320483); and polymers such as polythiophene,
`polyaniline, polythienylene vinylene, and polyphenylene
`vinylene (see JP-A No. 4-145192); and the like.
`[0011] HoWever, there are still problems at long-term
`operational stability, lifetime, luminescence brightness,
`luminous ef?ciency, and others. To overcome these prob
`lems, it is quite important to develop an inexpensive material
`having suf?ciently high optical and mechanical properties
`that is favorable in coating properties and suitable for mass
`production. In particular, devices containing a phthalocya
`nine derivative as a positive hole-injecting material have
`been Widely used because they are relatively better, but the
`injection ef?ciency is still unsatisfactory and the luminous
`ef?ciency of the devices remains to be improved. In addi
`tion, the phthalocyanine derivative, Which is used as a blue
`pigment, often caused the problem that absorbing a red
`emission light, changed the emission color and decreased
`the luminous ef?ciency. Use of other loW-molecular Weight
`positive hole-injecting materials also often carried the prob
`lem that the devices are inferior in stability and heat resis
`tance because of their loW glass transition and melting
`points, While use of polymer positive hole-injecting mate
`rials often carried the problem that it Was difficult to form a
`uniform ?lm by Wet casting and the lifetime of the device
`Was shorter. Phosphorescence devices particularly superior
`in internal quantum efficiency are attracting attentions
`recently, and for improvement of the ef?ciency thereof, it is
`necessary to develop a stable material for positive hole
`injecting layers.
`[0012] The condensed polycyclic compounds described in
`the invention (see e.g., E. Clar, W. Kelly, D. G. SteWart, J.
`
`W. Wright, J. Chem. Soc., (1956), 2652; Tokita, Arai,
`Ohoka, Nishi, Nippon Kagakukaishi JP, 1989, (5), 876; J.
`Photopolym. Sci. Technol., 11, 41 (1998); Tokita, Arai,
`Toya, Nishi, Nippon Kagakukaishi JP, 1988, (5), 814;
`Tokita, Suga, Toya, Nishi, Nippon Kagakukaishi JP, 1988,
`(1), 97; Mol. Cryst. Liq. Cryst., 1994, Vol. 246, 119; R.
`Schmidt, W. DreWs, H.-D. Brauer, Journal of Photochem
`istry, 18 (1982), 365; Daisuke Goma, Masao Ken, Sumio
`Tokita, Journal of Photopolymer Science and Technology,
`14, 2(2001), 239] have been studied in detail as a photo
`chromic material that changes its color by irradiation of a
`particular light or by application of heat, but there is almost
`no report on application thereof to organic electronic parts,
`and the kinds of the derivatives investigated are limited; and
`thus, there eXist an urgent need for a neW material.
`
`[0013] In addition, for production of a compound having
`the basic skeleton represented by Formula (1) or (2)
`described beloW by conducting ring closure of a compound
`having the basic skeleton represented by Formula (8) or (9)
`described beloW, a method of melting and ring-closing a
`compound in anhydrous aluminum chloride and sodium
`chloride (for eXample, E. Clar, W. Kelly, D. G. SteWart, J. W.
`Wright, J. Chem. Soc., (1956), 2652); a method of melting
`and ring-closing a compound in anhydrous aluminumchlo
`ride, sodiumchloride, andhydroquinone (e.g., JP-A No.
`6-56777 and Tokita, Arai, Toya, Nishi, Nippon Kagakukai
`shi JP, 1988, (5), 814; R. Schmidt, W. DreWs, H.-D. Brauer
`Journal of Photochemistry, 18 (1982), 365; and Daisuke
`Goma, Masao Ken, Sumio Tokita journal of Photopolymer
`Science and Technology, 14, 2(2001), 239), and other have
`been reported. HoWever, all of these methods Were not
`proper as a commercial method, as the ring closure reactions
`are inferior in Workability because they are carried out in the
`absence of solvent and the methods give chloride salts of
`Formula (1) or (2) as byproducts.
`
`DISCLOSURE OF THE INVENTION
`
`[0014] The inventors have found that it Was possible to
`overcome the problems above mentioned by using a par
`ticular condensed polycyclic compound as the material for
`light-emitting devices, in particular as the light-emitting
`material, and completed the invention.
`
`[0015] Accordingly, the invention provides a light-emit
`ting material (host and doping materials) for a light-emitting
`device higher in luminous efficiency that emits an orange to
`red light and a White light-emitting devices, and a light
`emitting device emitting a high-brightness and high-color
`purity light; and the light-emitting device according to the
`invention operates at loW voltage and has a high luminous
`ef?ciency as Well as practical stability and lifetime. In
`addition, the neW condensed polycyclic compound provided
`by the invention is useful as an organic electronic material
`and, in particular, as an organic EL material.
`
`[0016] More speci?cally, the invention provides: 1. A
`light-emitting device emitting light by electric energy hav
`ing one or more layers of organic thin ?lms formed betWeen
`an anode and a cathode, characteriZed in that the organic thin
`?lm contains a compound having the basic skeleton repre
`sented by the folloWing General Formula (1) or (2):
`
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`

`
`US 2006/0051612 A1
`
`Mar. 9, 2006
`
`(1)
`
`(2)
`
`X1
`
`X2 I
`
`0 X3
`
`X4
`
`(wherein, X1, X2, X3 and X4 each independently represent
`an oxygen, sulfur, selenium, or tellurium atom, or NR29; and
`R29 represents a hydrogen atom, an aliphatic hydrocarbon
`residue Which may be substituted, or an aromatic residue
`Which may be substituted.);
`
`[0017] 2. The light-emitting device described in 1 above
`mentioned, Wherein the compound having a basic skeleton
`represented by Formula (1) or (2) is a compound represented
`by the folloWing General Formula (3) or (4):
`
`(3)
`
`-continued
`
`(4)
`
`(Wherein, X1, X2, X3 and X4 each are the same as those in
`Formulae (1) and (2); R1 to R28 each independently repre
`sent a hydrogen atom or a substituent group; and the
`neighboring groups among the substituent groups repre
`sented by R1 to R14 and R29 in Formula (3) and R15 to R29
`in Formula (4) may bind to each other forming a ring(s)
`Which may be substituted.);
`
`[0018] 3. The light-emitting device described in 2 above
`mentioned, Wherein X1, X2, X3 and X4 in Formula (3) or (4)
`each represent an oXygen or sulfur atom;
`
`[0019] 4. The light-emitting device described in 2 or 3
`above mentioned, Wherein the neighboring groups among
`R1 to R4, R8 to R11, R15 to R18, and R21 to R24 in Formula (3)
`or (4) bind to each other, forming a ring(s) Which may be
`substituted;
`
`[0020] 5. The light-emitting device described in any one of
`2 to 4 above mentioned, Wherein R1 and R2 and/or R3 and R4
`and/or R8 and R9 and/or R10 and R11, and/or R15 and R16
`and/or R17 and R18 and/or R21 and R22 and/or R23 and R24 in
`Formula (3) or (4) bind to each other, forming an aromatic
`ring(s) Which may be substituted;
`
`[0021] 6. The light-emitting device described in any one of
`2 to 5 above mentioned, Wherein the substituent groups
`represented by R1 to R29 in Formula (3) or (4) each are a
`substituted or unsubstituted aliphatic hydrocarbon residue or
`a substituted or unsubstituted aromatic residue;
`
`[0022] 7. The light-emitting device described in any one of
`2 to 6 above mentioned, Wherein the substituent groups
`represented by R1 to R29 in Formulae (3) and (4) each are a
`halogen atom, an aromatic residue having a halogen atom, or
`an aliphatic hydrocarbon residue having a halogen atom;
`
`[0023] 8. The light-emitting device described in 7 above
`mentioned,5 Wherein the halogen atom is a bromine or
`?uorine atom;
`
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`
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`
`[0024] 9. The light-emitting device described in any one of
`2 to 8 above mentioned, Wherein X1 and X2 in the compound
`represented by Formula (3) each independently represent an
`oxygen or sulfur atom; R1 I represents H, F, CH3, Ph, or CF3;
`R2 represents H, CH3, C2H5, t-C4H9, Cy, Ph, MPh, Np, Th,
`Py, OCH3, OPh, F, Cl, Br, I, CN, N(CH3)2, CHO, COOH,
`COOCH3, COOPh, COPh, or CF3; R3 represents H, CH3,
`C2H5, t-C4H9, OCH3, OPh, N02, OH, F, CF3, CZFS, or Ph;
`R4 represents H, CH3, C2H5, t-C4H9, Cy, Ph, MPh, Np, Th,
`Py, OCH3, OPh, F, Cl, Br, I, CN, N(CH3)2, CHO, COOH,
`COOCH3, COOPh, COPh, or CF3; R8 represents H, F, CH3,
`Ph, or CF3; R9 represents H, CH3, C2H5, t-C4H9, Cy, Ph,
`MPh, Np, Th, Py, OCH3, OPh, F, Cl, Br, I, CN, N(CH3)2,
`CHO, COOH, COOCH3, COOPh, COPh, or CF3; R1O
`represents H, CH3, C2H5, t-C4H9, OCH3, OPh, N02, OH, F,
`CF3, C2F5, or Ph; R11, represents H, CH3, C2H5, t-C4H9, Cy,
`Ph, MPh, Np, Th, Py, OCH3, OPh, F, Cl, Br, I, CN, N(CH3)2,
`CHO, COOH, COOCH3, COOPh, COPh, or CF3; and R5 to
`R7 and R12 to R14 each are H (Wherein, Ph represents a
`phenyl group; MPh, a 4-methylphenyl group; Np, a naphthyl
`group; Th, a 2-thienyl group; Py, a 2-pyridyl group; and Cy,
`a cycloheXyl group.);
`
`[0025] 10. The light-emitting device described in any one
`of 2 to 9 above mentioned, Wherein the organic thin ?lm has
`a laminate structure at least containing a positive hole
`transporting layer and a light-emitting layer;
`
`[0026] 11. The light-emitting device described in any one
`of 1 to 10 above mentioned, Wherein an anode, a positive
`hole-transporting layer, a light-emitting layer, an electron
`transporting layer, and a cathode are laminated in that order;
`
`[0027] 12. The light-emitting device described in any one
`of 1 to 11 above mentioned, Wherein at least a positive
`hole-injecting layer, a positive hole-transporting layer, and
`an electron-transporting layer are formed betWeen the anode
`and the cathode;
`
`[0028] 13. The light-emitting device described in any one
`of 1 to 12 above mentioned, Wherein the compound having
`the basic skeleton represented by Formula (1) or (2) is
`contained as the host material of the light-emitting material
`in the light-emitting layer;
`
`[0029] 14. The light-emitting device described in any one
`of 1 to 13 above mentioned, Wherein the compound having
`the basic skeleton represented by Formula (1) or (2) is
`contained as the dopant for the light-emitting layer;
`
`[0030] 15. The light-emitting device described in any one
`of 1 to 14 above mentioned, Wherein a White light is emitted
`by combined use of a blue to green light-emitting material;
`
`[0031] 16. The light-emitting device described in any one
`of 1 to 15 above mentioned, Wherein the positive hole
`injecting layer described in 12 above mentioned contains a
`compound having the basic skeleton represented by the
`Formula (1) or (2);
`
`[0032] 17. The light-emitting device according to any one
`of 1 to 16, Wherein the light-emitting device is a device for
`a display in a matriX mode and/or a segment mode;
`
`[0033] 18. Acondensed polycyclic compound, represented
`by Formula (5):
`
`(5)
`
`(Wherein, R30 to R43 each independently represent a hydro
`gen atom, a halogen atom, an alkyl group Which may be
`substituted With an aromatic residue, an aromatic oXy group,
`an alkyloXy group, or a halogen atom, or an aromatic residue
`Which may be substituted With an aromatic residue, an
`aromatic oXy group, an alkyl group, an alkyloXy group, or a
`halogen atom; at least one of R30 to R43 is a halogen atom
`or an aromatic residue Which may be substituted With an
`aromatic residue, an aromatic oXy group, an alkyl group, an
`alkyloXy group or a halogen atom; and the neighboring
`groups among R30 to R43 may bind to each other forming a
`ring(s) Which may be substituted, hoWever excluding the
`case Where R30 and R31 and R37 and R38, or R32 and R33 and
`R39 and R40, bind to each other forming unsubstituted
`benZene rings and all of R30 to R43 that do not form a ring
`are a hydrogen atom.).
`
`[0034] 19. The condensed polycyclic compound according
`to 18, Wherein tWo or more of R30 to R43 each are a halogen
`atom or an aromatic residue Which may be substituted With
`an aromatic residue, an aromatic oXy group, an alkyl group,
`an alkyloXy group, or a halogen atom;
`
`[0035] 20. The condensed polycyclic compound according
`to 18 or 19, Wherein the substituent groups R34, R35, R36,
`R41, R42, and R43 on the compound represented by Formula
`(5) each are a hydrogen atom; R30 and R37 each represent a
`hydrogen atom, a halogen atom, or a C1 to C4 alkyl group;
`R31, R33, R38, and R40 each represent a hydrogen atom, a
`halogen atom, an aromatic residue, a thienyl group, or a C1
`to C4 alkyl group; and R32 and R39 each represent a hydro
`gen atom, a halogen atom, or a C1 to C4 alkyl group;
`
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`

`
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`
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`
`[0036] 21. A condensed polycyclic compound represented
`by Formula (6):
`
`[0039] 24A condensed polycyclic compound represented
`by the folloWing General Formula (7):
`
`(6)
`
`(7)
`
`(Wherein, X3 and X4 each independently represent an oXy
`gen,sulfur, selenium, or tellurium atom, or NR72; R72 rep
`resents a hydrogen atom, or an aliphatic hydrocarbon or
`aromatic residue Which may be substituted With an alkyl
`group, an alkyloXy group, an aromatic residue, an aromatic
`oXy group, or a halogen atom; R58 to R71 each represent a
`hydrogen atom, a halogen atom, an alkyl group Which may
`be substituted With an aromatic residue, an aromatic oXy
`group, an alkyloXy group or a halogen atom, or an aromatic
`residue Which may be substituted With an aromatic residue,
`an aromatic oXy group, an alkyl group, an alkyloXy group,
`or a halogen atom; at least one of R58 to R71 represents a
`halogen atom, an alkyl group Which may be substituted With
`an aromatic residue, an aromatic oXy group, an alkyloXy
`group or a halogen atom, or an aromatic residue Which may
`be substituted With an aromatic residue, an aromatic oXy
`group, an alkyl group, an alkyloXy group or a halogen atom;
`and the neighboring groups among the substituent groups
`R58 to R72 may bind to each other forming a ring(s) Which
`may be substituted.);
`
`[0040] 25. A method of producing a condensed polycyclic
`compound having a basic skeleton represented by the fol
`loWing General Formulae (1) and (2):
`
`(1)
`
`(Wherein, R44 to R57 each independently represent a hydro
`gen atom, a halogen atom, an alkyl group Which may be
`substituted With an aromatic residue, an aromatic oXy group,
`an alkyloXy group or a halogen atom, or an aromatic residue
`Which may be substituted With an aromatic residue, an
`aromatic oXy group, an alkyl group, an alkyloXy group or a
`halogen atom; at least one of R44 to R57 is a halogen atom,
`an alkyl group Which may be substituted With an aromatic
`residue, an aromatic oXy group, an alkyloXy group or a
`halogen atom, or an aromatic residue Which may be substi
`tuted With an aromatic residue, an aromatic oXy group, an
`alkyl group, an alkyloXy group or a halogen atom; and the
`neighboring groups among R44 to R57 may bind to each
`other forming a ring(s) Which may be substituted);
`
`[0037] 22. The condensed polycyclic compound according
`to 21, Wherein tWo or more of R44 to R57 each are a halogen
`atom, an alkyl group Which may be substituted With an
`aromatic residue, an aromatic oXy group, an alkyloXy group
`or a halogen atom, or an aromatic residue Which may be
`substituted With an aromatic residue, an aromatic oXy group,
`an alkyl group, an alkyloXy group, or a halogen atom;
`
`[0038] 23. The condensed polycyclic compound according
`to 21 or 22, Wherein the substituent groups R48, R49, R50,
`R55, R56, and R57 of the compound represented by Formula
`(6) each represent a hydrogen atom; R44 and R51 each
`represent a hydrogen atom, a halogen atom, or a C1 to C4
`alkyl group; R45, R47, R52, and R54 each represent a hydro
`gen atom, a halogen atom, an aromatic residue, a thienyl
`group, or a C1 to C4 alkyl group; R46 and R53 each represent
`a hydrogen atom, a halogen atom, or a C1 to C4 alkyl group;
`
`DUK SAN NEOLUX
`EXHIBIT 1024
`PAGE 000007
`
`

`
`US 2006/0051612 A1
`
`Mar. 9, 2006
`
`-continued
`
`BRIEF DESCRIPTION OF THE DRAWINGS
`
`(2)
`
`[0042] FIGS. 1 and 2 are schematic sectional vieWs
`illustrating the layer structure of a light-emitting device
`according to the invention.
`
`BEST MODE FOR CARRYING OUT THE
`INVENTION
`
`[0043] The light-emitting device, the compound, and the
`production method according to the invention Will be
`described in detail respectively.
`
`[0044] The invention relates to a light-emitting device
`Which emitting light by electric energy having an organic
`thin ?lm containing a positive hole-transporting layer, an
`electron-transporting layer, and others formed betWeen an
`anode and a cathode, characteriZed in that the organic thin
`?lm contains a compound having at least the basic skeleton
`represented by the Formula (1) or
`[0045] Compounds having a basic skeleton represented by
`Formula (1) or (2) of the invention Will be described beloW.
`In Formulae (1) and (2), X1, X2, X3 and X4 each indepen
`dently represent an oXygen, sulfur, selenium, or tellurium
`atom, or NR29. R29 represents a hydrogen atom, an aliphatic
`hydrocarbon residue Which may be substituted, or an aro
`matic residue Which may be substituted. The compound
`having the basic skeleton represented by Formula (1) or (2)
`may have one or more substituent groups, and the substitu
`ent groups may bind to each other, forming a ring(s).
`EXamples of the compounds having the basic skeleton
`represented by Formula (1) include the compounds repre
`sented by Formula (3) beloW, and eXamples of the com
`pounds having the basic skeleton represented by Formula (2)
`include the compounds represented by Formula
`[0046] The compounds represented by Formulae (3) and
`(4) of the invention Will be described in detail.
`[0047] In Formulae (3) and (4), X1, X2, X3 and X4 each
`independently represent an oXygen, sulfur, selenium, or
`tellurium atom, or NR29, and may be the same as or different
`from each other. Preferably, each group is an oxygen or
`sulfur atom or NR29, and more preferably an oXygen or
`sulfur atom. R29 represents a hydrogen atom, an aliphatic
`hydrocarbon residue Which may be substituted, or an aro
`matic residue Which may be substituted. The aliphatic
`hydrocarbon residue Which may be substituted or aromatic
`residue Which may be substituted of R29 is the same as the
`aliphatic hydrocarbon residues Which may be substituted or
`aromatic residue Which may be substituted of R1 to R28
`described beloW.
`[0048] R1 to R28 each independently represent a hydrogen
`atom or a substituent group, and the neighboring substituent
`groups may bind to each other, forming a ring(s) Which may
`be substituted. The substituent group represented by R1 to
`R28 is not particularly limited, and eXamples thereof include
`aliphatic hydrocarbon residues Which may be substituted,
`aromatic residues Which may be substituted, a cyano group,
`an isocyano group, a thiocyanato group, an isothiocyanato
`group, a nitro group, acyl groups, halogen atoms, a hydroXyl
`group, substituted or unsubstituted amino groups, alkoXyl
`groups, alkoXyalkyl groups, aromatic oXy groups Which may
`be substituted, a carboXyl group, a carbamoyl group, an
`aldehydo group, alkoXycarbonyl groups, aromatic oXycar
`bonyl groups, and the like. Among them, aliphatic hydro
`
`characterized by ring-closing a compound having the basic
`skeleton represented by the following General Formula (8)
`or (9):
`
`(8)
`
`(9)
`
`(Wherein, X1, X2, X3 and X4 are the same as those described
`above.) in the presence of a sulfonic acid compound; and
`
`[0041] 26. The method of production described in 25
`above mentioned, Wherein the sulfonic acid compound is
`sulfuric acid, an alkylsulfonic acid Which may be substi
`tuted, or an aromatic sulfonic acid Which may be substituted.
`
`DUK SAN NEOLUX
`EXHIBIT 1024
`PAGE 000008
`
`

`
`US 2006/0051612 A1
`
`Mar. 9, 2006
`
`carbon residues Which may be substituted, aromatic residues
`Which may be substituted, a cyano group, a nitro group, acyl
`groups, halogen atoms, a hydroxyl group, substituted or
`unsubstituted amino groups, alkoxyl groups, aromatic oxy
`groups Which may be substituted, and the like are preferable.
`Aliphatic hydrocarbon residues Which may be substituted,
`aromatic residues Which may be substituted, a nitro group,
`halogen atoms, substituted or unsubstituted amino groups,
`alkoxyl groups and the like are still more preferable; and
`among them, aliphatic hydrocarbon residues Which may be
`substituted or aromatic residues Which may be substituted
`and halogen atoms are particularly preferable. Most prefer
`ably are aromatic residues Which may be substituted, and
`among the aromatic groups, phenyl groups Which may be
`substituted are more preferable. Compounds having multiple
`aromatic residues Which may be substituted, in particular
`multiple phenyl groups Which may be substituted as the
`groups, as any of R1 to R28 groups are more preferable.
`[0049] Examples of the aliphatic hydrocarbon residues
`Which may be substituted include saturated or unsaturated,
`straight-chain, branched-chain, or cyclic aliphatic hydrocar
`bon residues Which may be substituted, and the number of
`carbons thereof is preferably 1 to 20. Examples of the
`saturated or unsaturated, straight- or branched-chain ali
`phatic hydrocarbon residues include methyl, ethyl, propyl,
`isopropyl, n-butyl, iso-butyl, allyl, t-butyl, n-pentyl, n-hexyl,
`n-octyl, n-decyl, n-dodecyl, n-stearyl, and n-butenyl groups,
`and the like. Examples of the cyclic aliphatic hydrocarbons
`include cycloalkyl groups having 3 to 12 carbon atoms such
`as cyclohexyl, cyclopentyl, adamantyl, and norbornyl
`groups. These aliphatic hydrocarbon residues may be sub
`stituted additionally With any one of the substit